When I was just a theatre kid in my senior year of high school, my friend’s dad pulled me aside. He was the CEO of a publicly traded tech company and (surprisingly to me) genuinely interested in our theatre lives. Not just “what’s the name of the skit you’re working on” interested. He wanted to know our favorite acting techniques, our audition monologues, and the conservatory programs we were applying to.

“You know, my wife and I met in theater school.” He tells me one afternoon. “Best training we ever had for business. You’re going to make one heck of a businessman someday.”

I’d never felt so insulted in my life.

Because what I heard, obviously, was: you’re going to be one heck of a failed actor.

Fast forward a decade. I’ve got a theater degree from UCLA, a graduate degree in acting from Delaware, and I’m living my dream as an actor in Chicago when a grad school friend calls. She needs help with a professional development course for a company downtown and thinks I’d be a great fit. She says, “It’s basically about using an actor’s voice in a business leadership environment.”

I think of the insult from high school. I say yes.

She mentions the company’s name. It’s McKinsey. I say, “Who are they? What do they do?” That was my business acumen in 2007.

Turns out the “insult” bore truth. And as an Executive Coach over the past close to two decades — with clients on six continents virtually, five in person; having taught storytelling and leadership development programs at Harvard Business School and Harvard’s Executive Education programs — I’ve landed on this truth: the way you show up when you’re speaking says more about what you’re saying than the words themselves.

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Most founders spend 99% of their prep time on what they’re going to say. I’m here to shift some of that focus from the ‘what’ to the ‘how’.

Table of contents

• What “engaging presence” actually means

• The 55-38-7 breakdown that changes everything

• The inform paradigm is killing your pitch

• Actor’s intent: the framework I use with every founder

• What about the five-minute pitch?

• Show up now

What “engaging presence” actually means

When I ask people what they notice when someone walks into a room with an engaging presence, I always get variations on the same list: eye contact, a smile, energy, the pace of their walk. Physical things. Visible things.

But the most important observation in that list is always the one you can’t see: how they’re listening. You feel it. You can’t put your finger on it, but you can tell when someone is genuinely tuned into the room versus when they’re waiting for their moment to speak.

There’s something else, too. When someone is truly engaged, it’s contagious. They smile, and then you’re smiling. They lean in, and the whole room leans in. One person’s presence can lift the energy of everyone around them — not because they performed, but because they were present.

Some of the traits we associate with engaging presence — warmth, expressiveness, ease in a crowd — do come more naturally to extroverts. I won’t pretend otherwise. Getting your energy from connecting with other people gives you a built-in advantage here.

But some of the most compelling communicators I’ve ever encountered are deeply introverted. And what I’ve found is that when an introvert chooses to show up with that kind of presence — because it doesn’t come instinctually — the impact is often more powerful. People can tell they’re making an effort. It lands differently.

The 55-38-7 breakdown that changes everything

Decades ago, a Professor at UCLA named Albert Mehrabian conducted a fascinating study which, in essence, answered the following question: What allows communication to last in the absence of the speaker?

Is it the content itself? The power of your voice? Your body language?

He found it wasn’t equal. It was 55% body language, 38% voice, and 7% content.

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My wife is a statistician. She was not pleased when I showed her that slide. Yes, it makes it look like you can ace the test with barely any content at all!

But that’s not the takeaway. The takeaway is this: the 93% — how you use your body and your voice — is what gives your audience access to the 7%. It’s not either/or. Your delivery isn’t separate from your content. It’s the vehicle for it.

Here’s the problem I see in almost every pitch, every board presentation, every keynote: founders spend the overwhelming majority of their prep time on the content side. The deck. The data. The structure. And then — maybe — at the last minute, there’s a passing thought: “That guy in the webinar said something about gestures. Maybe I’ll try that.”

A small shift here can make a massive difference. What if you spent 93% of your prep time on the content instead of 99%? And then spend the rest on how you’re going to use your body and voice to connect with the room?

I’d be out of a job. But your pitch would be a lot better.

The inform paradigm is killing your pitch

Let me show you what most decks look like as a communication framework:

Present the problem. Explain why it exists. Show the current market solutions. Explain why they’re failing. Provide evidence that customers are desperate for a change.

Present. Explain. Show. Explain. Provide.

Read that list again. Notice anything? There’s no change. It all sounds the same. And if how you’re saying things isn’t changing, you’ll lose your audience’s attention.

This is what I call the inform paradigm. And it’s where most founders live by default.

Now compare it to this: Instead of presenting the problem, you invite your audience to experience the problem. Instead of explaining why it exists, you alarm them. Transform your deck from one that informs to a story that moves your audience to action.

Actor’s intent: the framework I use with every founder

When actors approach a piece of text, they don’t ask: Should I say this line loudly or softly? Should I slow down here? Those are self-focused questions. They get you in your head. And the moment you’re in your head, you’ve lost your audience.

Actors ask a different question: how do I want this person to feel?

I’ve been using this technique — what I call actor’s intent — with founders for close to a decade. The idea is simple. Before you speak, don’t think about delivery mechanics. Think about your intention with the audience. Do you want to challenge them? Intrigue them? Alarm them? Encourage them? Command them?

I have a thesaurus of action verbs that I literally use as my mouse pad. It’s that central to my work.

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The verbs on that list aren’t neutral — they’re alive. When you speak with the intention to alarm someone, something changes about how you use your body and voice without you having to think about it. The intention does the work.

But here are two words that are specifically not on my curated list: “inform” and “educate.”

Those aren’t intentions, they’re outputs. They tell you what you’re delivering, not how you’re connecting. You can inform someone by encouraging them, intriguing them, or even amusing them. But you can’t just decide to “inform” someone and expect your audience to feel anything.

Putting it into practice

One of the founders in the masterclass I recently did on this topic with Not Another CEO walked me through his opening pitch. It was clear, well-structured, and forgettable. He hit all the right points. He told me about his company, their tech, their enterprise clients. Clean. Logical. Completely in the inform paradigm.

So I asked him: why do you care about this problem? He’d spent time as a head of marketing working with agencies. I pushed him to get specific. What made it hell?

He lit up. He told me about being bombarded with 40-page PDFs full of vanity metrics. About agencies hiding their failures. About feeling confused and helpless while watching consumer marketers just... thrive.

That’s a pitch. That’s a person. The information didn’t change, the humanity did.

When I asked him to redo the opening with that foundation, he started with: “I remember when I used to be in your shoes.” Six words. Everything changed. As one participant put it: “It completely shifted from here’s someone trying to sell me something, to here’s someone trying to help.”

Different audiences need different intentions

In another moment from the session, a founder was pitching his AI consulting practice. His default was to encourage and excite, and he did it beautifully. But his warmth was so consistent that it created a kind of flatness. There was no change.

I asked him to try a different intention: command. Tell your audience they need to act now. Make them feel urgency.

He was uncomfortable with it. Command felt out of character, almost aggressive. But he tried: “All of us are going to be replaced: either by AI, or earlier by someone who is using AI. Your business will be disrupted by newcomers who build everything with agents. If you don’t do it now, your lunch will be eaten by someone else.”

The room felt it. Someone said there was conviction — and that they felt compelled to hire him, not scared of him. Another said: “I actually felt urgency.”

The CEO’s reaction: “It’s a little hard, but I’m sure I can get used to it.”

That discomfort is the point. If you only pull from a handful of intentions, you’re not creating change. And without change, your audience drifts.

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The introvert question

Almost every time I do this work, someone asks: can introverts actually do this? Is this just a personality thing?

Here’s my honest answer: there’s probably a built-in advantage for people who get energized by connecting with others.

But I’ve watched introverts become exceptional communicators precisely because they’re so purposeful about it. When someone who doesn’t always lead with warmth or energy shows up with both, it lands harder. People feel the effort. They feel chosen.

What about the five-minute pitch?

One of the more practical questions I get is about time. If making it personal takes time — if you’re reenacting your origin story, building geography between pain and solution — how does that fit in a five-minute window?

A few things.

First, you need different versions. Two minutes, five minutes, 10 minutes, 30 minutes. Know what you’re cutting and why for each.

Second — and this is crucial — I don’t want you to do your whole pitch in five minutes. I want you to leave breadcrumbs. The goal of a short pitch isn’t to cover everything. It’s to make someone want to ask you questions. If you’ve made them feel the pain, and you’ve hinted at your traction, and you’ve told them you’re raising to get from 10 logos to 100 — that’s a breadcrumb. The phrase “tell me more” is worth more than another minute of you talking.

Here’s the uncomfortable truth about why VCs give you five minutes: people are not good at pitching. And so investors do the worst thing possible — they give you less time, which makes the pitch worse. Your job is to be good enough that investors want more time with you.

And you will hear ‘no’. A lot. But that’s part of the job. Your job is to pitch. Your job is to be comfortable hearing ‘no’ while being confident you’ll hear ‘yes’. And when you get your ‘yes’... you get to go back to your job of running the company.

Show up now

What I’ve learned from working with thousands of leaders across six continents is that the people who move rooms — who close their Series A after months of struggle, who turn skeptical VCs into believers, who get their teams to actually follow them — are not the ones with the best decks. They’re the ones who’ve learned to show up.

They don’t perform. They don’t fake it. They show up authentically.

In Mike Lipkin’s words:

Who you are being when you’re saying what you’re saying; says more about what you’re saying than what you’re saying.

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You already know how to access an engaging presence. You’ve done it. Think of the conversations where you felt fully alive, where the room was with you, where time disappeared. That version of you is already there. The work is learning to access it on purpose — with a VC who’s seen a hundred pitches this week, in a board room where the stakes are high, in a customer call where you need them to feel the problem before they’ll ever buy the solution.

If this work interests you, I’m easy to find. My email is markdannenbergcoaching@gmail.com, and I’m always happy to connect with founders.

We held ourselves to an extremely high standard of strategic coherence, and we revalidated that strategic coherence over and over again, especially through the early years of the company. And that intellectual honesty with ourselves about does our strategy makes logical sense in light of all of the changing inputs and new facts. — Marcu Ryu

That’s Marcus Ryu, Co-founder and former CEO of Guidewire. His company transformed the insurance industry and grew into a public company generating over $1.5 billion in revenue.

If you’re on a calendar fiscal year, you’re exactly halfway through it. And if you’re in the US, you’re heading into one of the quietest stretches of the year outside of Thanksgiving and Christmas. This is a rare opportunity to get out of the weeds and actually assess how your business is doing.

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In my experience, 100% of the time, you’re not where you thought you’d be. Some things are ahead, and some things are behind. That’s okay. The problem is when you don’t stop to honestly account for it and readjust your plan for the second half accordingly.

Here’s exactly what you need to be thinking about and doing this time of year.

Table of contents

• Take stock of where you are

• Decide what to change in the second half of the year

• Communicate the changes

Take stock of where you are

You’ve been in the weeds for six months. You might not even know what’s happening in and around your business. This is the time to zoom out and evaluate where things are.

Ask yourself these questions to better understand the state of your business:

• Is the top-line revenue where you expected? Did you get there the way you expected?

• Is churn or gross retention better or worse than planned? What are the driving factors?

• Did something shift in the market? A new competitor, an acquisition, a feature that landed differently than expected?

• Did you deliver a feature that wasn’t adopted? Did a small enhancement unlock a massive opportunity?

• Did you hire a game-changing employee? Did a key person leave?

• Did you think you were going to fundraise, and it didn’t happen? Did you end up raising earlier than expected? Did you raise more money than you planned?

You can’t improve what you don’t measure, and you can’t fix what you won’t face head-on. The CEOs who know something is off but decide to stay the course are the ones who dig themselves into a hole that gets harder and harder to climb out of.

Decide what to change in the second half of the year

Now that you know where your business stands, it’s time to look forward and implement the necessary changes. The time to change is now. Don’t wait, and don’t overthink it. Make the tough calls.

Ask yourself these questions to determine what you need to change:

• If your retention rate is behind the goal, is it realistic to get it back to where you originally thought it would be?

• Should you keep investing in that new product or feature you’ve been building for six months but haven’t delivered?

• Do you need to triple down on the small team focused on AI?

• Is that ICP still the right ICP? Are those territories still the right territories?

• Does something need to change in how your leadership team meets or how you run your company all-hands?

• Are there bets you made in January that aren’t paying off?

• Are there things working better than expected that deserve more resources?

Just because you committed to doing something at the start of the year doesn’t mean you should keep banging your head against the wall. Things change, and in today’s market, they change faster than ever. You can’t plan for a year and never stop to reassess, that’s just stupid. It’s the same reason the old school waterfall methodology fell out of favor. The world changes too fast for that.

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Communicate the changes

Once you’ve done the thinking, it’s time to rally the people: your co-founders, team, investors, customers, and partners.

Here’s how to get everyone on the same page:

• Start with your inner circle. Bring in your co-founders, your executive team and share what you’re seeing. Have them poke holes in your plan. They will most certainly catch things you missed.

• Align your board and investors. Even if the top-line number stays the same, if how you’re getting there has changed, you need to communicate that. The board and your investors care about the number, but they also care about what’s happening underneath it.

• Tell the company. Change is hard. Some people have a hard time with change, no matter what is changing. Your job is to build your team’s resilience around the change, help them understand why things are changing, and make it clear that this is the plan evolving, not failing.

• Inform external stakeholders: Your customers and partners don’t need every detail, but if something material has changed, don’t let them hear it through the grapevine. A proactive heads-up will build more trust than a reactive explanation.

Communicating the change can be scary, but you have to do this to survive. A lot of CEOs and founders see this as a failure. But if you do this right, you’ll earn more trust from your board, your team, and yourself than you would have by staying the course. Don’t pretend everything is on track just to avoid difficult conversations. That’s the path to failure.

The best CEOs never stop reassessing

July 4th is a rare vantage point. You’re exactly halfway through the year, and things are slowing down for a few days. You have the space to actually think. Use it. Take stock of where you are, decide what needs to change, and then communicate it. It’s not a failure to change the plan.

With all of that said, find a day, or at least half a day, to put your phone down and recharge. You won’t be 100% present no matter what you’re doing this weekend, but you can (and should) carve out some time to recharge.

I’ve interviewed dozens of VCs recently, and I’ve asked all of them point-blank: How long between that first meeting and deciding to invest?

Their responses ranged from 5 to 20 minutes, with an average of around 15 minutes. That’s what they say on record. I’m willing to bet it’s probably closer to 5 minutes across the board.

That doesn’t mean they’re writing a check on the spot. What they’re doing is deciding whether they like you, your idea, and the opportunity. The actual investment could take days, weeks, or even months. But you need to nail the first 5 minutes, or you’ll never get to the next step in the process.

When you walk into a meeting with investors, remember this: Investors hear dozens of pitches every week. You’re one of the many companies competing for their attention. But for you, this is one of the most important meetings of your life.

Investors are looking for the next generational company. They want the next Anthropic, OpenAI, or Cursor. And to get that, they’re looking for four things:

Can you survive the founder journey? Do you know something we don’t? Can you move faster than your competition? And is the market big enough to justify the risk?

What happens in the first 5 minutes is everything.

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Table of contents

• Why most pitches fail

• The 4 things VCs are looking for when you pitch them

• Why all four things matter

• This is how you pitch to investors

• How to know if your pitch is working

Why most pitches fail

The irony is that what makes pitches fail is often the opposite of what founders think will help them. You rehearse, polish, and memorize the presentation. But VCs are hearing dozens of pitches every week, and what really breaks through is authenticity and humanity, not necessarily perfection.

Here’s why they fail:

• You sound robotic and lack energy: You’ve given this pitch so many times, you can do it on autopilot. You hit your marks, deliver your slides, and it sounds polished. But the energy isn’t there. When that happens, VCs check out. This is your idea, this is the thing you’re dedicating your life to. They want to see the excitement behind that.

• You skip the personal story: You jump straight to the company, market size, product roadmap, and use of funds. But the best VCs want to understand you first. They want to know where you come from, why this problem eats at you, and what (and why) you’re trying to prove this idea.

• Weak storytelling: You have no narrative, no journey from problem to wedge, to massive vision.

And even if you’re avoiding these pitfalls, none of this matters if your product doesn’t actually solve a real problem or the market isn’t big enough.

Capturing their attention and getting them to lean in and really listen to you, that’s step one. If you don’t nail those first 5 minutes, you won’t get the chance to prove your product (or your vision for the product) is the real deal.

The 4 things VCs are looking for when you first meet them

In those first 5 minutes, investors are assessing the vibe they get from you, and they’re doing that by running through an unconscious checklist. Sure, there might be some nuance among investors, but in general, they’re looking for these things: grit, a competitive advantage, velocity in learning and shipping, and massive market potential.

1. Grit, passion, and resilience

The most important thing I’m really looking for is authenticity and a real passion for doing what they’re doing. I’m looking for that sign in the entrepreneur, that this is something they really, really care about. And that tells me they’ll never give up. – Jules Maltz, IVP

Can you survive the journey of a CEO? That’s the core question.

Building a company is brutal. It takes everything from you. At a minimum, you sacrifice sleep, time with family, mental health, and financial security. Most people burn out and quit when things get hard. Investors need to know you will keep charging forward, no matter what.

What they’re really looking for is a founder with a chip on their shoulder who wants to prove something to the world. They want someone so passionate and upset about the problem, who’s so driven to solve it, that nothing will get in their way.

They’re looking at your energy as soon as you walk in the room. They’re wondering how much you believe in solving the problem, and they want to see an intrinsic fire to succeed. They need to see that you, the CEO, have what it takes.

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2. Unfair competitive advantage

What’s your unique perspective on the problem? How long have you understood it? Where did you get your insight around that? – Amish Jani, FirstMark

Investors want to see that you know something about this space that others don’t.

Ian Sigalow, Co-Founder and Managing Partner at Greycroft, calls this an “earned secret.” You need to know something about the market, customer, the problem, or the solution that gives you an unfair advantage. It’s insider knowledge you’ve actually earned.

Maybe you’ve worked in this space for years and understand the customer’s pain better than anyone else. Maybe you’ve already solved this problem for a previous generation of technology, and now you’re solving it for the next one.

Maybe you know a regulation is coming that will reshape the market. Maybe you were a customer yourself and watched how the current solutions just don’t cut it. Or maybe you have a crazy strong network in the industry that can help you enter and navigate your market.

The main thing they’re looking for here is that you’ve earned the right to build this particular company in this particular space. You didn’t just wake up one day with an idea. You have context, experience, expertise, insight, and a strong hunch that the average founder doesn’t have.

3. Velocity of shipping and learning

We talk a lot about product velocity being the most critical metric we look for. – Jeff Morris Jr., Chapter One

Grit tells them you won’t quit. An unfair advantage tells them you understand the space. And velocity shows them how fast you move.

Speed used to be a nice-to-have, but in the AI era, speed is survival. Categories form and die in quarters. Investors need founders who can learn, iterate, and ship faster than their competitors. That’s how you get compounding progress.

Jessica Lin, Co-founder and General Partner at Work-Bench, shared this with me in the Not Another CEO podcast: “It’s better to be fast than to be right. If you’re fast (if you just have more at-bats), you’ll at least be able to course correct.”

Speed isn’t the same as passion. You can be passionate and slow. You can be resilient and stuck. But velocity is different. It’s how quickly you experiment, learn from failures, and change your course.

Rudina Seseri told me she looks for founders who do more than they say they’ll do between meetings. You tell her you’ll talk to 10 customers, and you show up to the next meeting having talked to 50.

It’s the founder who ships a new feature every week. Or the one who tests ideas ruthlessly, and moves with urgency because they know the window is closing. That’s velocity.

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4. Massive market potential

We’re looking for markets that are big enough. Zero to a billion in revenue. – Ian Sigalow, Greycroft

This is the last piece of the puzzle, and it’s a big one for VCs, for obvious reasons.

Venture capital doesn’t work like other investments. A VC fund makes dozens or even hundreds of bets. Most of them fail. Some do okay. But the fund can be massively successful if just a couple of those bets win.

That means they’re not looking for a nice, sustainable business that does tens of millions in annual revenue. They’re looking for something that could be a generational company worth billions of dollars, and last the test of time.

Here’s a LinkedIn post I saw recently that breaks down hypothetical numbers on what VCs are looking for. Read the full post here.

This doesn’t mean your idea has to be perfect or revolutionary. But they need to see that the market you’re going after is big enough and that you want to swing for the fences. The problem you’re solving needs to affect millions of people or billions in lost opportunity. It needs to be so big that if you win, you win big. Because if you win big, your investors win big.

Why all four things matter

It’s hard to hit all four in the first 5 minutes, and different investors will weigh things differently based on their experience and what they’re looking for. But across every investor I’ve talked to, these are the four things they’re evaluating. Sometimes consciously, sometimes unconsciously.

You could have an intense grit and a massive market opportunity, but if you don’t have an unfair competitive advantage, you’re just another founder chasing a big idea. You could have deep expertise in your space and be moving at lightning speed, but if the market isn’t big enough to return 50-100x, VCs won’t touch it.

And you could have all the velocity and curiosity in the world, but without the resilience to survive the brutal journey of a CEO, investors will fear you’ll quit when things get hard.

In those first 5 minutes, investors are evaluating you and your idea for all four. They’re asking themselves, “Can I believe this person will survive? Do they know something I don’t? Can they move fast enough to win? Is the market big enough to make this worth my time?”

If you’re completely missing one, that’s a problem. But if you can show genuine passion for all four things while staying true to who you are, you give yourself the best shot at getting them to lean in.

This is how you pitch to investors

I’ve worked with hundreds of founders on their pitches who have raised over $500m combined, and I’ve personally raised over $200 million. This is how I suggest structuring the first ~5 minutes of your meeting with investors.

Keep in mind, every pitch looks different, and you need this to feel natural, not robotic. But this flow works. Try it during your next pitch and see how they respond.

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First, start with your personal story

Don’t lead with the company. Lead with you. Tell them who you are and why this matters to you personally. This is where you show them why you are the right person to build a company and solve this specific problem. What did you experience that gave you the intrinsic motivation to build this company?

Did something in your childhood spark your entrepreneurial spirit? Did you face a personal challenge that shaped your resilience? These are the stories that matter. It’s the real personal stuff that explains who you are and why you won’t quit when things get hard.

Take them from context (who you are, where you come from) to realization (the problem that really bothers you) to decision (your decision to solve this).

Then, transition to your vision

Now paint the picture. In your wildest dreams, what does this thing become? Not just a number. What’s the massive, world-changing version of this idea?

Don’t sound delusional, but don’t minimize it either. Show them you’re thinking big. This is hard, especially if you’re at the earliest stage of building. You might be wondering if you deserve this opportunity (imposter syndrome is real). But this is critical, and every VC is looking for it.

For example, Stripe’s goal was to build the internet’s financial infrastructure. Shopify’s mission was to make e-commerce better for everyone. These are clear statements of: if everything goes to plan, here’s what that leads to.

Finally, present the wedge (your entry point)

Here’s where you make your vision believable. You just painted this massive picture, and now you need to ground it in reality. You can’t solve the entire market on day one. You need to pick a specific pain point, a customer segment, or a certain entry strategy that lets you prove the concept.

This is your wedge, and it’s what gets your foot in the door. Show them how you solve this narrow problem better than anyone. This tells them you’re thinking big, but also thinking practically.

How to know if your pitch is working

If you can tell this story (your personal story, vision, wedge) and do it in those first 5 to 10 minutes, you’ll see the difference immediately.

If your pitch is working: They’ll lean in, stop checking their phone, and their eyes will light up. They’ll start asking questions (real ones, sometimes hard ones, not the polite ones). They’ll be engaged and start brainstorming with you. The meeting wraps with the next one scheduled, and they immediately introduce you to more of the team. Or they ask about when you’re planning to close this round. These are all positive signals that your pitch is working.

You’ve lost them if: They’re clearly distracted, checking email, and glazing over details you feel are important. They might even fall asleep (it’s happened to me before). You can literally feel the energy in the room drop. The meeting wraps with no discussion of next steps or future meetings. They might even ask you to come back after you have a lead investor or once you get more traction. These are signs you’ve lost them.

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The main thing is to capture their attention and interest, and you have to do that faster than you realize because at this stage, you’re just another founder in a sea of others knocking at their door.

I think as much as 50% of people’s professional success is due to luck.

I’ve discussed this with many founders and CEOs, and while many of them agree, they usually respond with something like, “Yeah, but you can create your own luck.” And I fully believe that. But even if we do everything we can to “get lucky”, it’s still luck.

I’ve seen a terribly run company doing $4 million in questionable revenue sell for $400 million in cash, only to be shut down by the acquirer after a year. Why? Because the market they were in got hot all of a sudden. The incumbents were all rushing to enter the space, and this company happened to be featured on a list of top companies in the space that a junior person at a VC firm probably put together after a quick Google search. Suddenly, there’s an acquisition opportunity. That’s luck.

There’s a great LinkedIn post from the Twilio AE who closed Uber as an early customer. Thanks (in large part) to Uber’s explosive growth, Twilio grew rapidly. While there’s some strategy there, and Twilio obviously built a very useful product, no one could have guaranteed that Uber would become a household name and that its use case would generate tens of millions in annual revenue for Twilio.

There were companies building remote-work products that had limited adoption, customers, and revenue before COVID. Some were barely funded, or their revenue had plateaued. Then the pandemic hit. Suddenly, they accelerated 5 to 10 years of expected revenue growth into months or quarters. Why? Because everyone was forced to work remotely overnight, and companies were spending a ton of money trying to figure out their remote-work tech stack.

These are all examples of luck driving business and real outcomes.

But for every company that gets lucky, there are many more that don’t. I’ve seen a lot of founders build useful products, generate revenue, and execute really well… but they miss the liquidity window, run into a buzzsaw, lose to a better-funded competitor, or face a massive market shift. Then, they end up going into a death spiral or selling for a fraction of what they thought they’d get.

It’s usually easier to call luck when things go wrong (bad luck). But it’s much harder to admit when things go right, when you catch a wave, and everything works out.

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Table of contents

• Why we resist admitting luck

• The luck spectrum

• Creating luck conditions

• What happens when luck ends

Why we resist admitting luck

When you realize how much luck plays a role, you realize you don’t have as much control as you think. And then you start to resent other people’s luck. I’ve seen founders who were successful with their first company but not with their subsequent ones, even though they approach them the same way. There are a bunch of reasons this happens, but a big one is that they were lucky the first time and weren’t the second.

It’s hard to admit this because it makes us feel powerless, but acknowledging luck doesn’t mean giving up control. There’s a spectrum.

The luck spectrum: Types of luck and examples

When you look at all the luck that plays a role in founder success, you can break it into a few categories. Some of them, you have zero control over. Others, you have a bit more.

Macro dynamics and global events (zero control)

First, there are macro dynamics and world events. Things like interest rates, exit windows, market changes, and bubble timing – you can’t control this stuff. There are also global events such as wars, pandemics, and geopolitical dynamics that affect business. You have literally no control over this, and even the best struggle to predict it.

The dotcom boom is the perfect example. I know people who sold their company right before the bubble burst. Literally weeks before. Their company was doing a couple of million in revenue and was worth hundreds of millions of dollars. The next week, that same company was worth nearly zero.

This happened again in 2021. Companies were raising at 200 times their revenue. Were they worth that? No. But they thought they were. And now those same companies are crushed because the market has changed.

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Market and industry headwinds & tailwinds (limited control)

Then there’s your specific market. You have a little more control here in terms of choosing the right market to begin with, but the headwinds and tailwinds themselves? You can’t control those.

Say you start a cybersecurity company that addresses a vulnerability a bunch of companies have, and there’s a high-profile breach that exposes that exact vulnerability. Suddenly, demand for your product goes through the roof. Your lead flow explodes and your conversion rate spikes. You didn’t control any of that. That’s luck.

Or a big company like Google, Amazon, or Anthropic makes an acquisition or announces a product in your space that you didn’t know was coming. They have an unlimited budget and massive distribution you can’t compete with. But you didn’t see that coming, and now you’re fighting a battle you can’t win. That’s bad luck.

Customer dynamics (more control)

Then there’s your customer dynamics. Your customers are growing and scaling, and you’re riding that wave with them. The Twilio story I mentioned earlier is the perfect example. They got in with Uber. As Uber scaled, Twilio scaled. They didn’t do anything different. They just rode that wave.

You have more control here than you think, but you have to be smart about it.

Pick the right ICP, and target customers who are growing and will need more of your product over time. Build pricing and packaging that locks them in long-term. Those strategic decisions are how you position yourself for customer luck.

The flip side: You started a SaaS company in 2020 that only serves SaaS companies. Perfect positioning then. SaaS was hot, growing, and spending like never before. Then ZIRP ended. The SaaSpocalypse hit. Those same customers cut budgets and churned. Your churn goes through the roof, killing your company.

Team luck (most control)

Finally, there’s team luck. Sometimes you get lucky and hire that one person who changes the entire company. Or the person who comes up with the next brilliant idea, the next product, the next innovative campaign. You got lucky here, but you can actually position yourself to be lucky in this way.

When I became a CEO at 22, I hired from unconventional places like Craigslist and found people without much experience. Why? Because I was the CEO in my early twenties and didn’t know what I was doing, but I believed it was possible for others with little experience to be successful.

I see today that I was naive, and I got lucky. Many of those people came in, changed the course of the company, and grew into executive positions.

There are ways to control this type of luck, though, by improving your interview process and setting a higher bar for candidates across the board.

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Creating luck conditions

Seneca once said, “Luck is where preparation meets opportunity.” In other words, you can position yourself. You can be ready when opportunity strikes.

When I reflect on my own journey, I see where luck played a part. I can think of dozens of macro market tailwinds, coin-flip decisions that turned into huge wins, game-changing hires, and naive choices that worked out. All of it played a part in my success. Here are some of those moments. Maybe they’ll inspire you to position yourself to catch luck.

Taking meetings with junior investors

Everyone I knew, including my existing investors, told me not to take calls from junior VCs. They told me it would be a waste of time and that I should only focus on senior partners. But I thought those junior people were smart, they worked at good venture firms, and maybe I’d learn something. So I took a lot of meetings with them.

One of those meetings was with a very junior person at Accel. We hit it off. They liked me and invited me to the office in Palo Alto to meet with a couple of other team members. When I got there, I ended up meeting with Arun Mathew and Rich Wong.

During that meeting, I was having trouble connecting my laptop to the conference room TV. Their Director of IT came in, and since Accel was a BetterCloud customer, he recognized the sticker on my laptop. He said he used BetterCloud, and Rich and Arun asked him to sit in on the pitch.

So, the Director of IT, Dixon Chan, who knew and used our product, was championing BetterCloud while I pitched Arun and Rich on investing in the company. He sat in on the entire meeting and helped me answer questions about the product’s value prop and share how customers actually use it.

Fast forward a few months, and Accel led our next fundraising round. If Dixon hadn’t entered the room, that might not have happened. And none of it would have happened had I listened to my investor’s advice and skipped the initial call.

Making myself indispensable

Fresh out of college, I had accepted a job at an investment bank in Lagos, Nigeria (yes, a long story, but I was very excited about the opportunity). Around that same time, a friend of mine convinced me to meet with a 15-person tech company in Atlanta for a marketing role. I met with them even though I thought I wanted to be in finance.

I ended up taking the marketing role with them – an unknown tech company in Atlanta, in a space I didn’t fully understand. It wasn’t the finance career I thought I wanted. But I loved the founders, and they convinced me to join.

I hit the ground running. I showed up early and left late, every single day. I did every task given to me faster than anyone else. Nothing sat on my desk. I listened to the founders, spent time with them, and executed everything to the absolute best of my ability.

The company wasn’t doing well, and within 6 months, they essentially let everyone go except an engineer and me. They made me CEO. I was 22 years old.

You could say I got lucky. And I did. But I had positioned myself for that spot by showing up, being curious, and giving it my all. I had done the work to put myself there. I also met Jon Hallett there, who became my mentor and ultimately brought me into Cloud Sherpas. He ended up becoming the executive chairman at BetterCloud.

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Facing my fear

I was terrified of public speaking. I avoided it at all costs. I turned down every speaking opportunity because I was so nervous about speaking publicly. And because I avoided it, I know for a fact I missed out on opportunities and luck early in my career.

But I made a decision to get better. I worked hard, became more comfortable, and improved my delivery. I went from turning down every speaking engagement to taking every single opportunity that came my way. It didn’t matter if it was 10 people in a room or 700. I said yes to all of it.

One of those opportunities was a small meetup for Google customers in California. It was the kind of thing I would have avoided before. I flew out there to talk about SaaS trends in the ecosystem. A prospect in the audience heard me speak, came up to me afterward, and said they were fully aligned with the vision I was describing.

They became one of our biggest customers.

But none of that would have happened if I had kept saying no to public speaking opportunities. I had to put myself out there first.

What happens when luck ends (because it will)

Jules Maltz put it really well on the Not Another CEO Podcast:

“When the sun is shining on your business, that’s a great time to recruit super strong executives and think about act 2 and act 3 in your business.”

I know a company doing about $20 million in ARR. One customer (a Fortune 10 company) was responsible for $2.5 million of that revenue. They were crushing it, and they felt like they had done everything right.

Then we found out that this huge customer was building their own solution internally. They were going to leave.

The mistake the company made was failing to acknowledge that they were lucky to have that customer. They didn’t spend time with the customer and instead took the relationship for granted. When a customer is spending that much with you and regularly increasing their spend, you should realize that at some point, they might decide to buy from someone cheaper or build it themselves. But they didn’t see that risk coming. They assumed the relationship would always be there.

This happens all of the time. In 2021, companies raised money at valuations they didn’t deserve. Many of these companies burned through their cash. When the time came to pivot or invest in becoming AI-first, they couldn’t afford it. They’d either spent it all or convinced themselves they could just raise again at higher valuations (like they’d done before).

The smart (or maybe wise) founders are the ones who recognize when they get lucky. They squirrel away money and don’t spend recklessly or hire too fast. They use the good times to strengthen the foundation and build for the future. They recruit strong people. They play offense intelligently. They know the luck will end, and they’re ready for it.

If you’re lucky enough to be lucky, take advantage of it

Everyone experiences good luck and bad luck. That’s just life. The question is what you’ll do with luck when you find it. The real skill is recognizing when you’re lucky and maximizing that moment.

Lead with optimism, but internally, you have to be a bit of a pessimist. You need to be prepared for when luck ends. In fact, if you’re a little bit paranoid about luck ending, that’s a good headspace to be in. Don’t drink your own Kool-Aid and convince yourself you’ve already won.

The perfect market timing? It will probably go away. That game-changing person on your team? They might get recruited somewhere else. That amazing customer? They could build their own solution or switch to a competitor. Luck ends.

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So when it’s shining on you, acknowledge it and see it clearly for what it is. Don’t attribute it all to being good or smart. Take advantage of every minute of it. Lock in your customers. Pay your best people more. Keep reserves. Make decisions as if you know this lucky period won’t last forever, because it won’t.

The founders who understand this are the ones with a better chance of succeeding again and again. They don’t waste time resenting other people’s luck. They focus on positioning themselves for their own.

Trying to reach an enterprise buyer today is like trying to run up a mountain during an avalanche. AI-generated emails, automated LinkedIn requests, and a flood of vendors have made senior buyers nearly unreachable. Their inboxes are a war zone, and their patience is thin.

As a CEO, your job is harder than it’s ever been. Volume isn’t a strategy anymore – everyone has volume. What works is doing things that don’t scale.

I’m talking about account-based marketing using creative tactics that require real human effort.

Account-based marketing (ABM) is the practice of treating individual companies or people (not broad audiences) as their own market. Instead of casting a wide net, you identify specific target accounts and design personalized marketing and sales efforts around them.

ABM is really only worth it when your customers are paying you enough to justify the investment. As a rule of thumb, if your average contract value is below $50,000, most of these tactics don’t make sense.

I’ve spent years watching companies break through to accounts that seemed untouchable, and the ones that succeed almost always do it the same way: by doing something no one else bothered to do or was willing to do.

Here are eight account-based marketing examples I’ve seen work firsthand. They aren’t easy, and some of them are expensive. But that’s why they work.

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Table of contents

1. Send a gift that’s actually relevant and personalized

2. Create a once-in-a-lifetime experience

3. Start a podcast that spotlights your ideal buyer

4. Do deep research and make the pitch personal

5. Activate your champions (ask for referrals)

6. Host a confidential roundtable

7. Build a personalized demo environment

8. Let prospects choose their own experience

1. Send a gift that’s actually relevant and personalized

Corporate swag is the participation trophy of enterprise sales. To actually move someone, the gift has to be about them. This takes more work than ordering a standard Amazon card. You need to learn about them.

Look at their LinkedIn, check their Instagram if it’s public, read their interviews, and find the personal details.

Are they a fan of a particular sports team? Are they obsessed with their beard? Do they love mountain biking? Whatever it is, that’s your signal. Build the gift around those details, not around your brand. Send them tickets to a game or a new beard oil product. Make it personal. Make it about them.

The whole point is to give them something they can actually use and enjoy without feeling like a walking billboard. And the real win here is that they will always remember they got it from you. It’s two steps: find out what’s relevant to them, then personalize it. Local gift cards to a restaurant in their city beat Amazon or DoorDash every time.

I know a sales rep who found out their prospect was a UGA football fan and self-described girl-dad (he was even interviewed on a podcast about it). So they made him a custom UGA jersey with “girl dad” on the back. As soon as the prospect received it, they reached out to set up a call.

2. Create a once-in-a-lifetime experience

Every vendor is competing for the same calendar slots. But most sellers are doing the same thing: dinners and happy hours. If you want to get in front of someone who is genuinely hard to reach, you have to offer something they can’t access on their own and can’t bring themselves to turn down.

Think courtside seats to their team’s playoff game. Or midfield tickets to a World Cup match in their city. Or a reservation at a restaurant with a six-month waitlist. The bar is high, so you need to make it an experience that the person will want to go home and tell their spouse about.

The best example I have is a CIO dinner we hosted at Eleven Madison Park, when it was considered the world’s best restaurant. We spent $20,000, but we generated roughly $3 million in revenue from that one night.

We invited 15 people (ten prospects and five customers). We put everyone in a private room, assigned seats to make sure the right people were sitting next to each other, and placed swag bags at each chair. We had Patagonia jackets with a small BetterCloud logo on one arm (we’d collected everyone’s sizes ahead of time so they’d fit), branded t-shirts, socks, and a personalized handwritten note signed by everyone from our team who was there.

Again, no agenda, no presentation, no formal mention of our product. Just an extraordinary meal with the right group of like-minded people.

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What happened was more valuable than any sales meeting we could have scripted. We heard about the biggest challenges those buyers were facing, the vendors they were evaluating, and their goals for the year. And at the end of the night, one of our customers (the CIO of one of the most recognizable brands in the world) stood up unprompted and toasted BetterCloud in front of the whole room.

You can’t manufacture that moment, but you can create the conditions for it.

I remember a vendor selling to me who found an article I’d been featured in in the New York Times. They framed it and sent it with a handwritten note about what they’d taken from it. Their note said, “This is something that should be framed and hung up”. I hung it on my office wall and was reminded of them every time I saw it.

The key here is to be so relevant and personal that they never forget who sent them the gift.

3. Start a podcast that spotlights your ideal buyer

Most podcasts are built around the host. Build one around the prospect.

The idea is to create a show that spotlights the exact persona you’re trying to sell to. Don’t make it an opportunity to pitch. Make it a genuine platform that champions that person and their community. Then, invite your target accounts to be guests.

The pitch practically writes itself:

“We have a podcast that features the top [insert persona] in the world. We distribute it across all of our channels, and we want to feature you because of what you’ve built.”

That person will most likely say yes. You’re offering them a platform, exposure, and a feather in their cap. What you’re not doing is asking them to sit through a 30-minute demo.

Then you do the prep call before you record. Get to know them, their business, and their challenges. When you sit down to record, ask genuinely interesting questions. You need to create a conversation they’ll want to share. But at the same time, you can naturally weave in questions that surface discovery information that’s valuable to you as a founder.

Don’t interrogate them. Just have a real conversation that happens to be incredibly useful to your business.

After the episode goes live, promote the guest. Share their name and story with the world. Now they’re invested in your brand, whether they buy from you or not. And you’ve built a real relationship, not a sales interaction dressed up as one.

This works for prospects and existing customers. Either way, you’re adding value before you ever ask for anything in return.

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4. Do deep research and make the pitch hyper-personal

The goal here is to create a custom piece of content tailored to the prospect. The most obvious step is to customize your pitch for them. But take that same strategy further.

Use AI to conduct deep research on the prospect. Their business model, publicly stated challenges, competitive landscape, and the language they use to describe their priorities – all of this can be found through quick searches, and it’s gold. Find it and use it to your advantage. Merge that information with your content (case studies, whitepapers, and any other content you have or can create).

Don’t just create a generic one-pager. Create something that feels like it was written by someone who actually understands their world. There still needs to be a human in the loop to review and refine it, but AI makes the research and first draft much faster.

Want to go one step further? Use a tool like NotebookLM to turn that personalized research into a short audio podcast. It could be five to 10 minutes on how your product maps to their specific situation. People are actively doing this, and it’s working. I’ve seen it.

Most buyers aren’t going to block off 30 minutes to read a white paper, but they will listen to something on their commute, or while they’re walking the dog. You’re giving them the same information in a format that fits into their life.

The goal is to show up in a way that says, “I’ve done my homework, I understand your world, and I’m not here to waste your time.”

5. Activate your champions (ask for referrals)

Prospects who come through warm introductions are much more likely to become paying customers than cold leads. It all comes down to trust.

The play here is to identify your best customers (the ones who genuinely love your product and have seen real results) and turn them into a distribution channel. Ask them to make a single, specific introduction to someone they already know.

Here’s how it works. Identify one of your customers who’s a true advocate. Look at their network and identify someone who fits your ICP perfectly. Do your research on why that person would be a great fit for your product. Then write the introduction email you want your champion to send.

You say, “Hey, I’d love to get in front of this person. I think they’d get a lot of value out of what we’re doing. I’ve already written the email - would you be willing to send it?”

Most people who are happy with your product will say yes, especially when you’ve done all the work for them. And when they send it, make sure you thank them for the favor. Maybe it’s even a thank you with a small gift for helping you out.

The reason this works is the same reason cold outreach is getting harder: The noise comes from vendors, and the signal comes from peers. An email from a trusted colleague in the same industry carries more weight than anything your best SDR could write.

6. Host a confidential roundtable

There’s a version of this that looks like a sales event, and a version that actually works. The difference is whether you make it about you or them.

The version that works is simple: gather a small group of relevant leaders around a topic they genuinely care about. Not a product demo, not a panel where your company is front and center. Make it a real conversation between peers who have something meaningful in common (same function, same stage, same challenge).

Keep it small, off the record, and make sure there are no competitors in the room. Those three things are what make people actually show up and talk.

The best one of these I ever hosted was a CIO dinner in San Francisco. There was no agenda, and no pitch. Just a curated group of leaders in a room, and a topic worth discussing. One CIO in the room ended up sharing in detail what he did with his internal systems before taking his company public – not something you typically get to hear about first-hand.

Two others in the room were preparing to go public. The conversation was so valuable to them that they followed up afterward to go deeper. Another CIO talked about a new role they were adding to their team (something the others in the room hadn’t even thought about yet), and suddenly everyone was trading notes on what that person should cost and what skills to look for.

That’s the kind of conversation that doesn’t happen at a sales event. But it happens when you create the right environment.

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Most people think they need to be an expert to make these types of events happen. Wrong. You just need to be a connector. You need to identify the right people, put them in the same room, and create conditions for good conversations.

Do that consistently, and you’ll become someone people associate with that topic, industry, and community (even if you never say a word about your product). That kind of positioning is hard to buy and impossible to fake.

7. Build a personalized demo environment

The idea is simple: before you ever ask for a meeting, show up having already done work on their behalf.

Take everything publicly available about your target account (their website, LinkedIn presence, brand colors, logo, product details, 10-K if they’re public, case studies, whitepapers, pricing) and use it to build a version of your product that looks and feels tailored to them.

Of course, this works better for some products than others. For some, you can build a fully functional environment with their data. For others, it might just be a front end. Either way, it shows them you did the work, and that’s what stands out.

Then, record a short Loom walkthrough of the customized environment that walks through exactly how your product solves their specific problems. Send it via LinkedIn. Response rates to personalized videos are significantly higher than cold emails because they’re more personalized and show real effort.

This tactic isn’t new. Companies have been doing versions of this for years. What’s changed is how fast you can execute it. AI has made the research, the build, and the personalization much faster, which means there’s less excuse not to do it.

For example, a SaaS company selling to e-commerce brands could mock up improved product listings for prospects and send them over.

I heard about a company that builds websites for small brick-and-mortar businesses by scraping everything available on the business, like photos and reviews from Google, Yelp, etc. They take that information and the content, merge it with their existing website, and send a fully built site to the prospect with a link to “buy” the new website.

8. Let prospects choose their own experience

Most prospect events fail before anyone shows up. You pick the venue, the format, and the date, then blast out a generic invite to hundreds or thousands of prospects and customers. And then you wonder why the response rate is low, and the room feels thin. The problem isn’t the event. It’s that you chose it for yourself.

The fix is simple: ask them what they would be excited to do and when they’re available.

If I had 500 target accounts in New York City, I’d send them a short email that says something like:

“I want to invite you to an event, but I know you get invited to a lot of events. So I want to invite you to one you’re interested in and available to attend. Let me know which one sounds most interesting to you, and we will make it happen. ”

Then, give them a few options… a whiskey tasting, dinner, axe throwing, a baseball game, whatever makes sense for that specific audience. Give them a set of dates to choose from for when they can attend. Make it as easy as possible for them.

Two things happen. First, you get real data on who’s interested and what they want. Second, the people who register will actually show up and actually want to be there. You’re not herding reluctant attendees into a room they half-heartedly agreed to. You’re filling a room with people who raised their hands and want to be there.

Think about it from the other side. If someone invites you to a dinner and you’re an introvert who hates being seated next to strangers, you’re going to find a reason to cancel. But if that same person had asked you first and you said, “I’d love to go to a basketball game,” you’d be looking forward to it.

The main goal is to meet people where they are (or want to be), not just where it’s convenient for you.

None of this works if your product doesn’t

These tactics aren’t a shortcut. If your product is a vitamin (a nice-to-have, or easy to deprioritize), no amount of personalized videos or once-in-a-lifetime dinners will save you. You’ll just have a very expensive pipeline that doesn’t close.

But if your product is a painkiller (if it solves a real problem for a specific type of buyer), then getting in the door is 70% of the battle, especially these days when there’s more competition and copycats than ever. These eight examples exist for that scenario. When you know you have the right product for the right persona, and you just need to get in front of them.

None of these tactics is easy, and most of them require serious time, creativity, and money. But they work when your product solves a real problem. The tactics that scale are the ones everyone is already doing. The ones that work are the ones most people won’t bother with.

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Key takeaways

• Enterprise buyers are drowning in vendor noise, and the only way to cut through is to do things that don’t scale.

• The best ABM tactics require real human effort, creativity, and oftentimes real money. That’s why they work.

• Personalization only lands when it’s genuinely about the prospect, their brand, their interests, and their world.

• The signal comes from peers, not vendors. Warm introductions and roundtables work because trust is already there.

• Getting in the door is the hardest part, but none of this matters if your product doesn’t solve a real problem.

FAQ

What is account-based marketing? Account-based marketing (ABM) is the practice of treating individual companies as their own market. Instead of broad campaigns aimed at a wide audience, you identify specific target accounts and design personalized outreach and experiences around them.

Is ABM only for enterprise companies? Not necessarily, but it’s most effective when your average contract value is high enough to justify the time and cost involved. The tactics here are best suited for B2B companies selling to mid-market or enterprise buyers.

How much does ABM cost? It varies widely. A personalized Loom video costs almost nothing. A dinner at a world-class restaurant can run $20,000. The right investment depends on the size of the deal and how hard the account is to reach.

How do I know which tactic to use? Start with what you know about the prospect. If you have a strong customer advocate in their network, leverage that. If you have a product you can demo in their environment or with their brand materials, do that first. Match the tactic to the relationship and the opportunity.

How is ABM different from traditional marketing? Traditional marketing casts a wide net and optimizes for volume. ABM flips that: fewer accounts, much higher personalization, and a much closer alignment between marketing and sales.

I’ve hired and watched others hire hundreds of people at early-stage companies. Over time, a clear pattern emerged. The top 5% of those people (the ones who defined the company and moved the needle to an outsized degree) consistently shared three attributes: strong work ethic and stamina, the hunger and ability to learn new things, and a sharp EQ (emotional intelligence and empathy).

At the early stage, there’s no brand recognition to lean on, no established processes, and no one holding your hand. Things are changing all the time. You might be months away from running out of money. You’re literally living on the edge of whether the company survives.

You need people who can jump in and execute.

Hire the right ones, and they’ll carry you forward, setting the bar high for other employees. Hire the wrong ones, and they’ll stunt your growth.

I’m going to share why these three attributes matter specifically at the early stage of building a company, and how to screen for them before you make the hire.

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Table of contents

1. A relentless work ethic and stamina

2. The hunger and ability to learn new things

3. A sharp EQ (emotional intelligence and empathy)

1. A relentless work ethic and stamina

You need your early employees to have the grit and stamina to do whatever it takes to get the job done. These are the people showing up to do the work when no one is watching, no one is asking, and nothing is easy. They should have the drive to outwork everyone around them.

My first company sold to very small business owners who would research vendors late at night after they finished their day, so there were plenty of incoming calls to be answered after hours. One of our reps would take his phone home at night and on weekends, plug it into his home network, and answer those calls. While everyone else was at dinner, he was closing deals.

He had more pipeline than anyone on the team and literally hit 3x his quota. He made the sacrifice and was willing to work after hours to help both the company and himself succeed. That’s grit.

One of the engineers at BetterCloud overhead me talking with someone on the team about a feature customers had been asking for – something that would help us close a big prospect. Without being asked, they spent the next two weeks working nights and weekends and delivered a fully built, ready-to-deploy version of something we’d been struggling to ship for months.

Another time, our customers were really pushing us for 24/7 support, but our entire team was on the East Coast. Instead of waiting for a solution, one of our support reps volunteered to flip his entire schedule. They started sleeping during the day and working overnight so we could test out extended coverage without hiring offshore.

A little crazy? Maybe. But that’s the kind of person who thrives at the early stage.

Brute force is often the only path forward when you’re getting started. There’s no marketing engine behind you, no inbound pipeline, and no support structure. You’re probably understaffed, meaning everyone is wearing multiple hats. But the people who succeed are the ones willing to grind through it anyway.

This is partly why (after years of backlash) hustle culture is making a comeback. The 9-9-6 model (9am to 9pm, six days a week) was being discussed in startup circles a lot earlier this year. Some companies even openly advertise it as their operating model.

I’m not here to glorify this, but at the early stage, outworking is how you get momentum. You need to punch above your weight to get from zero to 1.

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How to screen for this

Ask this question: “What’s the hardest thing you’ve had to overcome in your personal or professional life?”

Then listen. Not just to what they say, but how they say it. The people who have been through genuinely hard things tend to have a resilience or a chip on their shoulder that’s hard to teach. You need people who are ready to go to battle for you.

The other move is to be upfront about the pace and reality of the job. Tell them what’s actually required. I’ve done this in interviews and watched people’s reactions tell me everything I needed to know. If they flinch, that’s useful information. You want someone who hears it and leans in.

2. The hunger and ability to learn new things

The second attribute is harder to fake: a genuine hunger to learn new things. Not just IQ or aptitude, but the actual desire to understand your industry, product, customers, and competitive landscape, even when none of it is inherently interesting.

The first company I ran sold phone systems to small businesses. Nothing too exciting there. But one of the best salespeople I ever hired made herself flashcards to memorize phone system terminology (PBX, VoIP, etc).

She studied those relentlessly, on her own, and without being asked. She would quiz herself on terms most people would never bother to learn. That way, even though this was her first job and she had no experience selling phone systems, she could speak with authority and answer questions accurately and confidently. That’s the mindset you’re looking for.

An engineer at another company spent a week sitting in the support queue, taking tickets as if they were on the support team. They wanted to understand firsthand what customers were experiencing and what it actually took to troubleshoot their problems. At the end of the week, they presented their findings to the entire engineering team.

I once challenged my entire sales team to do the actual work our customers were doing: log in to the product, go through the workflows, see what it felt like, and compare it to doing the same task manually without our product. One person did it. She came back having spent hours in a demo account, walking through real user workflows. She learned a ton about how people actually use the product and then integrated those insights into her conversations with prospects.

At one company, we were small and taking on a much bigger competitor. We were struggling to figure out how to position ourselves head-to-head against them. Someone on the team took it upon themselves to post as a prospect, book a demo with a competitor, and ask pointed questions about how the competitor positioned against us. In 30 minutes, they learned more than we could have gathered in weeks of research.

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Of course, today, with AI, a lot of that information is available nearly instantly. And that’s the thing: the resources to learn have never been more available than today. If someone isn’t using the information available, they don’t really want to learn. The ones who are hungry to learn are doing the extra work to close the knowledge gap.

How to screen for this

Start simple by asking: “What research have you done on the company so far?”

One of my mentors early on would open every interview with that question. If the candidate said no, he’d end the interview on the spot. It sounds extreme. But if someone is applying for a job and hasn’t looked at your website, do you really want to hire them?

You can dig deeper in a few ways.

If you have a PLG product, did they sign up and try it? The candidates who come in having already explored the product are showing you exactly how they’ll approach everything else on the job.

Listen to the questions they ask you. Generic ones signal they came in cold. Specific ones signal someone who did the work. Someone who says, “I listened to your podcast, and you mentioned X… I was curious about that,” is showing you how they approach their work.

You can also ask how they typically get up to speed in a new place. At the early stage, no one is handing them a training program. You want someone who knows how to figure it out on their own.

3. Sharp EQ (emotional intelligence and empathy)

The third attribute is the hardest to screen for and the easiest to overlook: EQ. This is the ability to genuinely understand what the person across from you is dealing with and adjust accordingly. This one is important, but often overlooked.

People with high EQ will build strong relationships, be good teammates, work well with early customers, and intuitively sense where to invest their time and energy.

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Think about what it means to sell to a CRO. That person is under constant pressure. CROs have one of the shortest tenures of any executive function because they’re always on the line. When you call them, you’re asking for time they don’t have, while others are constantly looking over their shoulder. The best salespeople understand that before they even pick up the phone.

The same goes for IT. The IT person is probably the most underappreciated and overworked person at most companies. They’re the ones keeping the lights on while no one notices. When you get them on a call, they likely have six fires burning at once. Do you respect that? Do you even know it?

I learned this the hard way early in my career. I heard a competitor of ours was meeting customers in person, so I reached out to an IT contact at a large company we were both trying to land and offered to fly out and take him to dinner. He said, “Dave, I don’t even like going to meals with my friends. I like your product, and it seems like it solves my problems, but I don’t need to go to dinner with you.”

That stuck with me. Reading the room means understanding who you’re talking to before the conversation even starts. You want a product manager who really listens to customers, understands their pain points, and connects with them. You want an engineering leader who understands the pressure your GTM team is facing as they approach the end of the quarter, still racing toward their quota.

The best go-to-market people I’ve worked with understand that in today’s world, nobody has to talk to you. They’re only on that call for one or more of these reasons: because they like you, trust you, or know they will get something out of the conversation.

One rep I worked with would find out a prospect’s favorite sports team before every call and show up wearing their jersey. It sounds like a small thing, but it worked because it was authentic. And that’s the key: authenticity.

Empathy that’s performed falls apart immediately. People see through it faster than you’d think. True top performers actually care about the person on the other side.

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How to screen for this

Ask the candidate: “Describe the value your last company delivered to customers.”

Do they recite a value prop, or do they actually embody the customer’s pain? Do they mention names? Do they share specific stories?

For GTM roles, ask which customer they had the closest relationship with. Do they refer to the customer as an account, a number, or a metric? Or do they tell you the person’s name, their company, and what they were working through?

The ones with real empathy remember the relationship and tell you the entire story.

If you find someone with all three, don’t let them go

I’d guess that only about 5% of candidates will have all three of these attributes. And that’s what makes them so valuable.

If you can find someone who does all three (works their ass off, learns whatever is thrown at them, and genuinely cares about the people they work with), hold on to them. I’ve written before about how to treat your top performers, and it starts with recognizing them.

And if you’re the one joining an early-stage company, this is your playbook. Show up with these three things, and you will stand out.

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2026 arrived, and Jones was doing great. We had been building a vertical software company for 9 years, and we were hitting our stride.

Q3 and Q4 of 2025 were our largest quarters in revenue history. We had crossed the 8-figure ARR milestone while doubling our sales and marketing efficiency and slashing monthly burn by 65% year over year. We’d just shipped the industry’s first AI Insurance Agent. We had 231 people across four global offices, protecting over 36,000 projects and properties from insurance risk across 2.7 billion square feet of real estate and construction.

And I handed over the CEO role to someone else.

If that sounds counterintuitive, it should. The conventional wisdom says founders step back when things get hard. A couple of missed quarters. An exhausted leader. A Board running low on patience.

I’m here today to argue the opposite: the best time to make a founder-led CEO transition is when things are working. And I want to share exactly how we pulled it off.

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Table of contents:

1. My company became the market leader

2. When private equity entered the picture

3. Three signals that it is time to transition

4. The mechanics of a clean CEO transition

My company became the market leader

In February 2017, my Co-Founder and CTO, Michael Rudman, and I won the AXA InsurTech Competition in Tel Aviv. We had a simple idea with a complex execution problem: construction and real estate companies were drowning in insurance paperwork, taking on enormous legal and financial risk because the process of verifying that contractors and vendors held the right insurance coverage was entirely manual, slow, and error-prone.

We believed AI could solve it, and most people in the industry had never thought about the problem long enough to disagree. But at the time, AI models were neither accurate nor sophisticated enough to solve the problem end-to-end. We made a bet on building the AI future.

What followed was nine years of building from scratch, shaping the category before the category had a name, and before AI took over the narrative in tech. We survived fundraising winters. We navigated a global pandemic. We dodged a national banking crisis. We made hundreds of wrong bets and a handful of right ones that defined our trajectory. The early years were a relentless test of whether the vision was real or whether we were just stubborn enough to keep believing in it.

By late 2025, the answer was clear: Jones had become the market leader for insurance verification in the built world, serving the country’s largest construction and real estate companies. Customers trusted us with their most critical workflows every day, at a scale I hadn’t dared to think about in 2017.

This is the company I handed off to a new CEO.

When private equity entered the picture

The chapter that most directly shaped the CEO transition wasn’t the product milestones or the record revenue achieved. It was the shift in our capital structure and one specific moment in Q1 2025 that made everything clear.

When a private equity group joined as our institutional partner in November 2024, it marked a meaningful transition in the company’s identity. Not just in capital structure, but also in mandate.

In the early days, our board was built for belief. Angels, venture funds, and strategic investors whose job was to back a vision before it was proven. The board’s risk profile essentially matched the founder’s: bet on the builders, stay the course, and survive to fight another day to have a shot at a billion-dollar (or higher) outcome.

When PE investors enter the picture, the calculus changes. PE doesn’t invest in potential; it invests in scalability, predictability, and profitability. The question at the board level shifted from “can you build it?” to “can you scale it profitably, and if so, on what timeline?” The institutional mandate became to fortify the core product, scale the GTM motion, expand margins, and build toward strategic optionality. Everything gets evaluated through that lens.

I understood this intellectually. But what I didn’t fully understand until Q1 2025 is what it would feel like as founder/CEO.

At the time, I was evaluating the board budget and ran into something I hadn’t experienced in nearly a decade of building Jones. It was an inflexibility that I couldn’t find my way around. Not hostility. Not indifference. This was something more disorienting than either: a set of norms and assumptions I didn’t fully recognize, an operating logic I was learning on the fly.

So I approached it the way I’d always handled hard problems with our venture investors. Roll up my sleeves, be transparent about the challenges, ask for advice and genuinely mean it, link arms and solve it together. It was the playbook that had worked for 8 years.

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But it didn’t work this time. Not because the board was wrong, or because my approach was flawed. But because I was speaking a language they did not share. They were esteemed scholars in their own PE literature. I was quoting from a different text entirely.

That was the major signal. A quiet, accumulating realization that the company had crossed into a different institutional phase, and my founder operating mode, the one that had worked for so long, was no longer the mother tongue of the room I was standing in.

It wasn’t that my skills had become irrelevant. It was that the company’s needs had become institutionalized, and that specificity started to matter more than the founder’s horsepower and creativity that had gotten us here.

Three signals that it is time to transition

If you’re a founder sitting with this question, wondering whether now is the right moment to welcome a new CEO, here’s a framework I wish someone had handed me in advance of raising a PE round. Your company will send you signals. You just have to know how to read them:

Signal 1: You’re winning on efficiency, not invention

For the first decade of Jones, our edge was creation. We were building a category from scratch, shipping AI products that didn’t exist, and growing by convincing the market that our vision was real. In that phase, the dominant risks were groundbreaking product, remarkable talent, exponential growth, and pure survival. The CEO’s job was fundamentally 0→1.

Once a vertical AI company reaches real institutional scale, the risks change. The business no longer wins primarily on invention. It wins on operational precision. Your best quarters start coming from improved conversion rates and tighter sales cycles rather than new product launches. AI stops being just a product differentiator and starts being a margin lever. For instance, at Jones, we saw a 30% increase in auditing volume alongside an 18% reduction in variable costs, producing a 13% jump in gross margins. Those were the priorities of the PE board.

Yeah, that’s the vibe. And you get used to it.

When this shift happens, the CEO’s job changes fundamentally. You’re no longer primarily an inventor. You’re an organizational designer and systems architect. If you love the former and aren’t naturally wired for the latter two, that asymmetry is worth taking seriously.

Signal 2: The round that changes the question

Here’s the thing about raising from PE: when you’re in the middle of a raise, targeting PE doesn’t feel like an existential question about your role. It feels like the next stage of capitalizing the business. One more chapter that you, the founder/CEO with continued energy and genuine motivation to build, are ready to write.

The term sheet doesn’t come with a warning label. Nobody sends you a note that says “this round may change what leadership this company needs”. You sign, you celebrate, and you keep building. And that’s exactly the blind spot.

Institutional investors have specific performance profiles they’re optimizing for. The question of whether you’re the right person to execute against those expectations is one of the most important acts of leadership. And yet it’s almost never the question you think to work through in the moment.

For Jones, the path forward required three things working in concert. Go-To-Market precision, AI-driven margin expansion, and strategic optionality for the board. Each required operational discipline that favored a PE-focused operator, someone who had navigated the model before and knew which levers to pull and when. I also needed to be honest with myself about whether this was the opportunity that I, as a founder, wanted to spend my time on.

In hindsight, that was clear. In the moment of the raise, it wasn’t what I was asking myself.

The tactical takeaway: before you close a PE round, find a few founders who have been through the same transition, someone post-PE, ideally post-CEO transition, and give them a specific assignment. Have them ask you brutally honest questions about whether you’re truly ready to operate in this new institutional context. Not the questions the term sheet is implicitly answering, but the questions it isn’t asking. You want them to reveal your blind spots.

That conversation, held before you sign the terms sheet, is the one I wish I’d had. Let me be clear: this doesn’t mean I wouldn’t have taken the money. It just means you go into it knowing more clearly what the company needs in the CEO, and whether you are the person for that future role.

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Signal 3: You have enough strength to choose

The first signal (that moment in Q1 2025 when I realized I was speaking a different language than my board) wasn’t a call to act immediately. It was a call to awareness.

The lesson isn’t to react the moment something feels off. It’s to recognize the signal, sit with it honestly, and then respond deliberately, with the company’s best interests at the center.

Because your decision isn’t about the founder. It’s about the company.

There’s an adage in tech and venture capital: always raise from a position of strength. It’s frustrating advice, as most often you’re not in that position. But it’s true. The same logic applies here. Founders should lead CEO transitions from a position of strength, and more importantly, they should actively manufacture the conditions for that window to exist.

That means continuing to perform well. Crush the board milestones. Get the team, the product, and the balance sheet into the best shape you can before you start the conversation. Because these conditions matter enormously. A new CEO walking into a business with momentum can attract great talent, earn the team’s trust faster, and build on what’s already working. A new CEO walking into a business under pressure is immediately playing defense.

We hit our window in late 2025. Record quarters. A healthy balance sheet. A world-class AI product in the market. A team that had proven it could execute at scale. That strength wasn’t incidental — it was the prerequisite. This gave our new CEO a running start and the company the best possible chance of making the transition work.

Founders owe this to the company, to their team, and to their investors. It’s not only stewardship. It’s the fiduciary duty. And it’s simply the right thing to do.

The mechanics of a clean CEO transition

Most people don’t write about “how” to transition. Once you’ve made the decision, the work of making it real begins.

We organized the transition around three layers: downloading founder intuition, handing off ownership, and aligning on the future.

Layer 1: Downloading founder intuition

For 8 years, most of the Jones strategy lived inside my head: Product strategy and logic, customer nuance, the cultural DNA. There was context behind every major decision that never made it into a slide deck. That tribal knowledge is an asset, and in a poorly structured transition, it evaporates. Here are two examples:

• The Product Vision: Our new CEO and I spent hours on the logic behind our AI roadmap; not just what we’re building, but why, and which parts of the vision are non-negotiable if we want to keep winning the category. We put that in writing. Not as a manifesto, but as a working onboarding document that the new CEO can interrogate, evolve, and reference when the inevitable trade-off decisions arrive.

• The Leadership Map: You can’t inherit a 231-person culture from an org chart. We mapped the key leaders and cultural carriers across the business, the people who shape how others think and behave, regardless of their formal title or seniority. Then we assessed where the incoming CEO’s operating style aligns with that culture, and where friction is likely to emerge. We also flew to every geographic hub to spend time with key leaders, both formally and informally. Getting honest about that gap early is far less expensive than discovering it at month four.

Layer 2: Handing off ownership

The fastest way to break a winning company is through ambiguous leadership. During a transition, if the team receives two different signals from two different leaders, execution stalls. We were deliberate about preventing that from day one.

We built a 3-month transition framework for this around two principles. First, autonomy: the incoming CEO owns the P&L, the GTM machinery, headcount and hiring, and the day-to-day operating rhythm – full stop. The team needed to know clearly and consistently that the buck stops with them, from day one.

Second, high-leverage focus. My role shifted to the areas where founder context provides irreplaceable value: areas like board governance, strategic partnerships, and our long-term AI roadmap.

The tactical takeaway is to map the founder’s domain and the CEO’s domain before you start the transition. Don’t leave it to evolve organically. Name it explicitly, put it in writing, explain it to your team, and revisit it at the 30, 60, and 90-day marks.

Layer 3: Aligning on the future

In a founder-led company, the team’s belief in the mission is often an extension of their belief in the founder. That trust doesn’t transfer automatically with a C-suite change. Trust has to be earned, and the founder has to actively enable the conditions for that to happen.

So to build that trust, we were intentional about three things:

First, co-signing the early moves: During the transition, we were deliberate about co-signing major strategic initiatives so the team sees that the new CEO’s decisions are a direct evolution of the vision, not a departure from it.

Second, explicit advocacy: My job during the succession was to be our new CEO’s most vocal advocate, specifically articulating why his superpowers were exactly what Jones needed for the new chapter.

Third, passing the mic: In meetings where I once led, I sat in the active listener seat. The new CEO took the final word, I provided historical context in the room and in post-meeting debriefs. This is harder than it sounds when you have strong opinions and years of context. But it’s the only way the team learns to orient toward the new leader.

Put the company ahead of yourself

Everything I’ve described — reading the signals, manufacturing the window, executing the handoff — requires putting the company ahead of yourself at every step. That’s not a minor ask.

That’s because founders are taught to think of themselves as the irreplaceable force holding everything together. And there’s truth in that, especially in the early years. But that narrative can become a trap.

The ultimate act of leading a company is not building something that depends on you. It’s building something bigger than you. Bringing on specialized leadership isn’t a retreat from that mission. Done right, it’s the fullest expression of it, a deliberate bet that the company’s future is too important to be constrained by any one person’s fixed set of skills, including your own.

The founder/CEO can leave, and that’s often how you build something that endures. But at the same time, the connective tissue, the values, and the tribal knowledge have to stay. When you’ve built something that holds together without you, you’ve succeeded, even if it feels like a loss.

If you are a CEO considering a transition, or whether it is time for new leadership, please don’t hesitate to reach out.

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Key takeaways

• The best time for a founder CEO transition is when the company is winning, not when it’s struggling. Strength gives the new CEO a running start.

• PE investment changes the institutional mandate. The skills that got you here (invention, vision, survival) may not be what the next phase requires (operational precision, margin expansion, scalability).

• Three signals it’s time: you’re winning on efficiency rather than invention, you’ve raised a round that changes the question, and you have enough strength to choose deliberately.

• A clean transition has three layers: downloading founder intuition into working documents, handing off ownership with zero ambiguity, and actively enabling the new CEO to earn the team’s trust.

• The ultimate act of founder leadership is building something bigger than yourself, and knowing when specialized leadership serves that mission better than you can.

Most companies already have leadership meetings. They’re just not effective. Here’s what I’ve seen after operating three companies and advising dozens of CEOs.

Communication across the leadership team happens through email, Slack, one-on-ones, short stand-ups a few times a week, and a longer weekly meeting that nobody wants to be in. The weekly meeting runs for an hour, gets canceled when people travel, and they always run out of time before getting to anything important.

Based on my experience, I believe 75% of leadership teams are not working in lockstep. They’re disconnected, working in silos, not aligned on priorities. They’re not accountable to each other, and they’re using you in a hub-and-spoke model.

I spent years running my first company like this. My CRO and I would discuss pipeline strategy in a one-on-one. Then I’d relay it to my CMO during our one-on-one (although some details got lost in translation). When those two met to coordinate, they were working off different versions of the same conversation.

Your company is only as effective as your leadership team. That’s why I push CEOs to invest the time, energy, and resources into a strong weekly leadership team meeting.

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Table of contents

• The leadership meeting you need

• Why this is your most important meeting

• Setting up your leadership team meeting

• The four-part leadership meeting agenda

• How this connects to your operating rhythm

The leadership meeting you need

When I say “leadership team,” I’m talking about your functional leaders (the people running each core function of your business). Early on, that might be managers or team leads, or maybe even individual contributors. Over time, it transitions to VPs and the C-suite. You’ll often have a mix of leadership levels in the room.

Title doesn’t matter. You need functional representation and an effective agenda.

But not the boring status update meeting where everyone reads numbers out loud. And not the meeting where people discuss a couple of projects and decide to schedule additional meetings to discuss them further.

I’m talking about a real leadership meeting where every functional leader in your company sits in the same room, hears the same information, debates the same decisions, and leaves aligned.

This is your most important meeting as CEO. It’s where you eliminate the hub-and-spoke chaos, and you tear down silos, where strategic initiatives get pressure-tested before they go to the company or the board, and where your leadership team actually becomes a team instead of a group of individuals reporting to you.

Why this is your most important meeting

Many leaders think their most critical meetings are the one-on-ones with each functional leader. These are important, but leadership team meetings carry significant weight. They connect cross-functional leaders, drive alignment, and save you time being the messenger.

It’s where alignment actually happens

When your CRO, CMO, CTO, or any functional leader at the time are all in the room hearing the same information at the same time, they’re less likely to walk away with different interpretations. When your head of customer success hears directly from the product team about what’s coming, why they prioritized it, and has a chance to ask questions, they can plan accordingly and empower their team to communicate more effectively with customers.

When everyone sees the same priorities, the same trade-offs, and the same constraints and risks, you don’t have to spend the next week realigning people who were never aligned in the first place.

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It turns your leadership team into an actual team

When your CTO presents a major technology infrastructure project to the full leadership team, they have to explain why it matters to the business, not just to the engineering team. When your head of sales asks for more headcount, they have to make that case in front of the CFO and discuss the trade-offs. This is how leaders learn to think beyond their function.

It’s where strategic work gets pressure-tested first

Every major initiative at your company should be discussed here first. Fundraising, M&A, the customer conference, and major product launches. If it matters to the company, it should get pressure-tested in this room first before it goes to the company all-hands or the board meeting. You get questions, you get pushback, and you get better ideas.

Then, by the time you do present to the company or the board, it’s been refined by the key leaders in your organization. You get all the context and all the decision-makers in the same room at once. That’s what makes the weekly leadership meeting irreplaceable.

Setting up your leadership team meeting

Here’s what you need to know before you schedule your first leadership team meeting.

When to start and who attends

Start this meeting once your company has leaders for each function, or most functions. That could be when the company is 25-30 people. Before that, you probably don’t need the formality of leadership meetings. In the real early days, the company is still small enough that a weekly all-hands meeting drives the alignment you need.

Title doesn’t matter, functional representation matters. Every person who is leading a function at your company should attend. If you have a customer success lead and no one above them, they should be in the room.

This group will change over time. You might have your director of sales in the room today, then hire a CRO who replaces them. That’s ok, and expected, just set this expectation upfront.

Logistics

Make this weekly and non-negotiable. This meeting shouldn’t get booked over. It doesn’t get canceled. If people are traveling or on PTO, they should be expected to read the meeting notes and/or watch the recording. That said, I recommend avoiding travel to accommodate the meeting. It’s that critical.

I suggest scheduling these Tuesdays at a time that works best for you and your team. Avoid Mondays. Too many long weekends and vacations that bleed into Monday. Let people catch up and start their week. You’ll also be asking them to submit their agenda items and updates in advance so attendees have time to review everything (ideally 24 hours before the meeting). Depending on company size, these meetings might take 90 minutes to 3 hours.

I recently spoke with a CEO who wanted to cap their weekly leadership team meeting at 60 minutes. The problem is that the entire meeting was people saying, “We’ll take that offline.” You need time for real conversations. I suggested he lengthen them, and he couldn’t believe how much more valuable they became just by giving the topics space to breathe.

Rules of engagement

Set these expectations explicitly:

• Everything discussed here is confidential unless decided otherwise.

• This isn’t a democracy; you want input, but you (the CEO) should make the final decisions.

• Everyone must speak up - create a safe space where people aren’t afraid to say what’s on their mind.

• Anyone with follow-up items is responsible for actually completing them.

• No use of phones or computers unless you’re using them for the meeting or there’s an emergency.

• The people in this room may change over time. The format and length may also change.

• The goal is alignment and accountability.

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The four-part leadership meeting agenda

Here’s how the meeting actually works. Stick to these four parts every week.

Part 1: Recurring items (30-45 minutes)

This section stays the same every week. Start by reviewing the top KPIs for the business. Then, have each functional leader share the following:

Highlights and headwinds

Ask your functional leaders to submit three highlights and three headwinds in the agenda doc, and have them come prepared to discuss one of each. Prior to the meeting, each leader should fill out their section of the agenda. This gives them time to think through what actually matters instead of making things up on the spot.

We used to do this verbally in the meeting, but people weren’t prepared. They rambled, and it took forever. Once we moved to written updates in advance, everything changed. People came prepared, they were concise, and we actually had time to discuss what mattered.

Priority changes

This is the “change order” section of the agenda, and it’s critical. When a big opportunity comes in, you can’t just decide to do it and expect everyone to get on board and absorb it. Think of it like a contractor working on your house. They can’t just show up and charge you extra. They have to have a conversation: “This wasn’t in the original plan, here’s the impact, here’s what it will cost, and here’s the tradeoff”.

Without this section, alignment gets destroyed because, in reality, things will change, and your leadership team needs to know about those changes first; otherwise, it all unravels. Prioritizing changes as a team forces everyone to see the trade-offs in real time.

Key meetings and milestones

This is a quick two-minute update on what’s happening this week. The upcoming board meeting, a flagship customer visiting the office, and the upcoming holiday that requires rescheduling the all-hands. You need to make sure everyone knows what’s on the calendar that affects them and their teams.

Part 2: Strategic topics (60-90 minutes)

This is the bulk of the leadership meeting, and that’s why it’s so valuable. Most leadership meetings only cover the recurring stuff, KPIs, and general updates. That’s not deep enough. The strategic topics section is where you actually get work done as a leadership team.

You’ll have 1-3 strategic topics each week based on what’s happening in the business. Different leaders present their topics (it’s not just you talking for 90 minutes). Each functional leader should come prepared to discuss their topic and share slides, reports, mockups, etc., with the team in advance so everyone has time to review and prepare questions.

When it makes sense, I love to bring in people who aren’t on the leadership team to present. Maybe your customer support manager presents CSAT improvements. Maybe your sales engineer presents on a technical POC. This is huge for development.

An important note: You’ll quickly build a backlog of topics. Don’t squeeze them all in. Give each subject the time it needs and keep reprioritizing. You’ll also have some regular items: board meeting prep, quarterly results review, and product roadmap updates.

Strategic topics typically fall into three categories:

Telling and answering questions

You’re not asking for permission or trying to change the plan. You’re informing the team and taking questions.

Example: Your board meeting is in three weeks. You walk the team through the agenda, the slides you need from each person, and the timeline. You’re not debating whether to have a board meeting; you’re making sure everyone knows what’s expected and can ask questions about their part.

Rough draft and feedback

You have a plan, but you want input to make it better.

Example: You’re implementing a new performance review process. You already know you’re doing reviews, you already know when, and you generally know the format. But you want the leadership team’s input on the specific questions to ask, how many people should provide feedback, etc. You’re refining the plan, not starting from scratch.

Brainstorming

You’re genuinely exploring options and want the team to help you think through it.

Example: You’re considering growing through acquisition. You want to discuss which category would move the needle the most for the company. Or you’re redefining company values and want the team to brainstorm what matters most. These are open-ended discussions where you’re building the plan together.

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Part 3: Follow-ups from last meeting (5-15 minutes)

This part is simple, and it’s all about accountability: What did we say we were going to do last week, and did we do it? If not, why?

Review the action items from the previous meeting and add new items to the follow-up list based on what came up in today’s strategic topics. If you have an EA or chief of staff, they might track the follow-up items. But the responsibility to deliver is on the person who committed to it. You shouldn’t have to remind people. They should come to the meeting ready to report on what they said they’d do.

Part 4: The elephant in the room (15-30 minutes)

End every leadership meeting with this question: “What’s the elephant in the room we’re not saying out loud?”

Most people treat leadership meetings like a routine. They agree because they don’t want to create conflict. They want to be easy to work with, and they worry they’re the only ones thinking something, so they stay quiet. Then, everyone walks out of the meeting, and the real conversation happens in the hallway or over Slack.

This section forces the conversation into the room.

Examples:

• “You said that feature was coming out a week late, but it’s now three months late. What’s different this time?”

• “We’re saying we’re going to hit that sales number, but the pipeline doesn’t look like it’s possible. Do we need to take a different approach?”

• “We just spent an hour talking about the customer conference, but I don’t think anyone actually believes we can pull this off with the current budget. Should we re-evaluate?”

This is where people say what they’re actually thinking instead of what they think they’re supposed to say.

The companies that do this well tell me it’s the most important part of the meeting. It creates space for honest conversations. It catches problems before they become disasters. It builds trust because people see that you actually want to hear what they’re thinking, not just what sounds good.

If you skip this section, people will walk out of your leadership meeting thinking one thing and saying another.

How this connects to your operating rhythm

The materials you create for your leadership team meeting become the materials for everything else.

When you discuss a strategic topic in your leadership meeting (customer conference planning, new product launch, company values, or a major partnership), you’re creating a deck or document to present it. That same deck or document (refined after your leadership team asks questions and pokes holes in it) becomes the content for your all-hands meeting, and a subset of it becomes content for your board meeting.

I used to spend three days putting together my board deck. Another CEO who was further ahead in his journey asked me, “Why don’t you just use the decks from your leadership team meeting?” I said, “What decks?” He said, “Don’t you have strategic topics you discuss?” I did, but I wasn’t thinking about it this way.

Once I started doing this, it saved me a lot of time and drove more alignment across the organization. If something was important enough to put in the board deck, we discussed it in the leadership meeting first. The team asked questions, challenged assumptions, and ultimately made it better. Then we presented it to the company at the all-hands meeting and finally, to the board.

Everything flows from this meeting

If reducing COGS is your company’s top priority right now, your CTO should discuss it in the leadership team meeting. If the most important thing is hitting your sales number, but the pipeline doesn’t support it, that should be a strategic topic. If you’re about to launch a major initiative, your leadership team should see it before anyone else.

This is how everything connects. When you have a real operating rhythm, these things aren’t separate; they’re the same pieces of information flowing through different groups of people.

The leadership meeting is where it all starts.

Key takeaways

• Your weekly leadership team meeting is more important than your one-on-ones, all-hands, and board meetings because it’s the only place where all your functional leaders hear the same information at the same time and can actually create alignment.

• Start this meeting when your company reaches 25-30 people. Every person leading a function should be in the room. Title doesn’t matter, functional representation does.

• Use this four-part agenda: recurring items, strategic topics, follow-ups, and the elephant in the room.

• The materials you create for this meeting can become content for your all-hands meeting and board deck slides. Discuss important topics with your leadership team first, then present refined versions to the company and board.

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FAQ

How long should a leadership team meeting be? 90 minutes to 3 hours, depending on company size. You need time for real conversations, not just status updates.

Who should attend leadership team meetings? Every person who is leading a function at your company, regardless of their title. You need functional representation across the entire organization.

When should I schedule leadership team meetings? Too many long weekends and vacations fall on Mondays. Same for Friday. Tuesday at 10:30 am or 11 am gives people time to catch up on Monday and start the week before jumping into strategic discussions.

When you close your first customer, there’s this overwhelming sense of relief. You did it. You got someone to say yes. They’ve signed the contract, and they’re actually paying for something you built.

And then you immediately move on to finding the next customer.

I’ve seen this happen with almost every first-time founder I work with. You put so much energy into landing those first deals that once they close, you’re already thinking about how to get the next one. It feels like momentum, and when investors are pushing you to hit ARR milestones and customer count targets, it makes sense to think this way.

Plus, in those early days, you’re not really dealing with churn yet. Everyone is in the first few months of using the product or year one of their contract. But if you don’t invest in turning those first customers into raving fans, you’re not just risking churn down the road, you’re missing a massive upside opportunity.

I’m talking about going above and beyond, doing unscalable things to make your customers feel valued and like they’re part of your company, from day one.

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Table of contents

1. Your first customers are the ones who help you build

2. The compound value of raving fans

3. Ask early customers what to build next

4. Assign a dedicated engineer to fix bugs immediately

5. Spend recurring 1:1 time with early customers

6. Hold their hand during implementation and onboarding

7. Amplify their personal brand

8. Go overboard with personalized swag

9. Ask for feedback on prototypes before building

Early customers are more like investors, not just buyers

Your early customers help you figure out what to build when you barely have a product. They’re the ones who will sit through bugs, missing features, and a clunky UI. They’ll give you feedback and forgive you when you make mistakes.

And if you do this right, your early customers will go to bat for you in several ways. They’ll be references for you (for other customers, investors, and partners), volunteer to participate in case studies and write reviews about you on sites like G2, and speak at conferences on behalf of your company.

These are the people who push you to add new features, they tell you what they’re seeing from competitors, and they become your eyes and ears in the market. They’re invested in your success in a way that customer number 500 never will be.

The compound value of raving fans

When you have that first set of customers who feel like they’ve been in the trenches with you, you get something most founders don’t realize they need until it’s too late: leeway to mess up.

Your product goes down for half a day? They stand by you. Renewal comes up, and the price increases 20%, 30%, or even 40%? They fight for the budget. A competitor reaches out with a cheaper alternative? They don’t take the call because you’ve already built trust and loyalty with them. Or even better, maybe they take the call to gather some intel, then share it with you.

This is the compound value. These relationships pay dividends for years.

That core group of early customers could be with you for 10 years, maybe more. Sometimes at the same company, often not. When they leave for their next role, you’re the first product they buy. They’ve already invested in you. They know the product works. They trust you and your team. So when they land at a new company and need to solve the same problem, they’re not evaluating five vendors; they’re going to you.

But they don’t stop there. They tell their colleagues and industry friends about you. They share your company on social media. They become word-of-mouth marketing engines for your brand.

If you do this right, these early customers will feel like they’re part of your story. They were there early with you, helping you build and being patient as you went through growing pains.

This is what’s on the line when you’re deciding whether to invest the time, energy, and money in making your first customers love you.

Here are seven ways to turn your first customers into raving fans.

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1. Ask early customers what to build next

You’ll hear tons of feature requests from early customers, and it will probably overwhelm you. Here’s how to figure out what to prioritize while also surprising and delighting them.

The key is letting your customers help you decide. Send a quick survey to all your current customers. “We’ve heard these 10 things over and over again. Which one do you think we should build next?” Make it clear that the feature that gets the most votes will be prioritized next.

Build whichever one gets the most votes. And this is the most important part: follow up with them and close the loop. When you ship the feature, email all of them and tell them it’s live. Tell them you built it because they voted for it, and thank them for pushing you to get it out.

It’s that simple, but you’ll be surprised how many companies fail to approach early product development this way. And when you close the loop, it establishes a level of trust and loyalty that can’t be matched.

Tip: Don’t put anything on this list that you’re not willing to build. This isn’t a fake democracy where you pretend to care about their input and then build whatever you want. You have to be ready to deliver.

2. Assign a dedicated engineer to fix bugs immediately

Every piece of software has bugs, and most software users expect them. This is especially true for new products. But what they don’t expect is for you to fix those bugs fast.

If you have someone dedicated to fixing bugs as soon as they come in, you create goodwill that’s hard to replicate any other way. Of course, many bugs can’t be resolved right away, but a lot can. Most companies don’t do this, and it’s an easy win for building trust and loyalty.

This doesn’t mean you need a full-time engineer dedicated to fixing bugs (but depending on your product, team size, number of customers, and the quality of your code, maybe you do). Having someone on call ready to jump in and resolve issues quickly is what matters. Maybe they even get on a call with the customer to recreate the bug and show they’re actively working on it.

Again, close the loop. Don’t just fix it silently and hope they notice. Tell them it’s done. That’s the whole play. Fix it fast, tell them you fixed it, and move on.

Tip: Have engineers on rotation in the support queue so customers can talk directly with the people who fix bugs. This creates a memorable experience for the customer and gives your engineers invaluable exposure to real user problems.

3. Spend recurring 1:1 time with early customers

As the CEO of a small startup doing very little in revenue, you might feel insignificant. You could go out of business tomorrow. Who cares about getting on a call with you, right?

Wrong. Your customers don’t get on calls with Zoom’s CEO, and they’re not talking to the CEO of Salesforce. When most of the products they use are from massive companies, having direct access to you (the CEO or founder, the person making product decisions) is a differentiation.

Your title matters, even if you feel like it doesn’t.

In the early days of BetterCloud, I was doing monthly hour-long meetings with our first customers. Then it moved to quarterly as we scaled, and it naturally became less frequent. But in those early days, that recurring time was critical.

These weren’t support calls. We talked about what we were building and why. We talked about what we were seeing in the market and what their peers (our other customers) were seeing. I’d share our roadmap and get their feedback. They’d tell me about their business priorities and where they were getting stuck.

All of this helps influence the roadmap, which is super important. But it also meant I could help them be more successful in their role.

I could tell them, “Other companies are approaching this problem this way,” or “Here’s what’s working for similar teams.” That kind of market intelligence is valuable for your product and for your customer relationships.

Tip: Make yourself accessible beyond those scheduled meetings. I’ve seen founders spin up shared Slack channels with clients where the entire engineering team can communicate directly with the customer. I’ve seen other CEOs give out their personal cell phone numbers.

4. Hold their hand during implementation and onboarding

Many customers, especially with an immature product, are going to struggle. Maybe the UI is bad. Or some product features are half-baked. Or critical functionality might be missing altogether, requiring manual workarounds.

This is normal for new products, but you can’t ignore those gaps. Your job is to make sure whatever problem they’re trying to solve with your product is actually achievable.

This is the forward-deployed engineer concept people talk about now. Sometimes it’s a consultant. Sometimes it’s a customer support person. The point is to hold the customer’s hand and provide whatever resources they need to be successful.

That might be helping them write custom integrations or building bespoke solutions for them on the fly. Or maybe it’s simply walking them through a workflow.

This doesn’t have to be you personally (although it might be). It could be your co-founder, CTO, or your first support hire. Whatever the case, someone needs to own making sure these customers are successful.

Tip: Don’t charge for implementation support. It’s too early at this stage. If these are your first customers, the ROI of them truly using your product and loving it outweighs any dollars you’d get from professional services or consulting. You want them in there, using it, seeing its value, and telling others about it.

5. Amplify their personal brand

This one is underrated. Many of the people you’re selling to (whether directors, managers, or individual contributors) have never had their personal brand out there in the world. They’ve never been featured in anything professionally. No one has ever asked them to do a case study, appear in a video, or talk publicly about their work.

So when you go to them and say, “We’d love to do a case study with you,” most founders frame it as a favor. “Would you be willing to help us out and lend your name to our company?”

Flip that around. Position it as, “We want to amplify you. You’re taking a unique approach here. You’re doing something forward-thinking that other people in your role should know about, and we want to feature that. We want to share it with other customers and potential customers.”

Do a case study, record a video, and post it on LinkedIn, tagging them. For a lot of people I’ve done this with, it’s the first time in their career that anyone has featured them or their work.

I had someone tell me once, “You did this. You put me out there. And I actually got a bunch of job offers because other people saw what I was doing at my company.”

You get a case study and social proof. They get career advancement and visibility. It’s not a favor, it’s a trade that benefits both of you.

Tip: Make it easy for them to say yes. Provide a brief on the key discussion points you want to include so they can come prepared, confident, and aligned on the narrative.

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6. Go overboard with personalized swag

This one sounds stupid, but it works.

Most companies handle swag the same way: They get the cheapest hoodies, slap their logo on them, and send them out. The customer gets it, says “thanks,” and it sits in a drawer forever next to all the other swag they’ve collected.

Do the opposite, get creative. Send them something that makes them feel special. Think limited-edition, personalized, and high-quality swag like a Timbuk2 backpack or Yeti Tumbler. It should be something they value and that they can tell you put serious thought into.

When we were a 10-person company, we printed 60 hoodies. We sent 50 of them to our first 50 customers and kept 10 for our employees. That’s it. Those were the only people who had that hoodie, and we told them that.

“Only the first 50 customers and our 10 employees have this hoodie. Thank you for being a part of this with us.”

We also took the time to write real thank-you cards and had everyone at the company sign them. Does this take time and money? Yea. But it’s about thoughtfulness.

I even sent swag to an entire IT leader once so they could distribute it to their entire team. They were so excited about it that they posted photos on social media wearing our gear. Years would pass, and customers would show up at our booth at conferences wearing the hoodie with our original logo, and they were so proud to show it off. You can’t buy that kind of organic visibility.

Tip: Spend more than you feel comfortable with. Get creative with it, and do something unexpected. You don’t always need to do this, but in the early days, this is a great way to stand out, make an impact, and be memorable.

7. Ask for feedback on prototypes before building

Let’s say a customer requests a feature in one of those monthly calls. Great. You agree it makes sense to build, and you add it to the roadmap.

But there are hundreds of different ways you could build that feature. Instead of just going off and building based on your best guess, interview them, and then show them a clickable prototype. Have other potential users click through the prototype and get their feedback and do this before you write a single line of code.

This does two things:

First, you get actual product insights. You find out whether your approach solves their problem or if you’re missing something. You catch issues before they become expensive rebuilds or lead to disappointed customers.

Second, they feel valued and involved. They’re not just requesting features and hoping you build them correctly. They’re actively shaping how those features work. That reinforces the idea that they’re part of building this product with you.

It’s collaborative instead of transactional, and that difference matters.

These things aren’t scalable, and that’s okay

You can’t do monthly CEO calls with 1,000 customers. You can’t send personalized swag to every user. You can’t have a dedicated engineer fixing bugs for every single person who reports one.

But you don’t have to do these things forever. You have to do them now, in the early days.

What you’re really building here isn’t just happy customers. You’re building your company’s DNA and culture. You’re establishing how you treat people, how you think about customer relationships, and what you’re willing to invest in to make people feel valued.

That becomes embedded in who you are as you grow. It sets the standard for how your team operates in the long term. And in markets with 100 copycats and new competitors spinning up faster than ever, this is how you stand apart.

Your competitors can copy your features, and they can undercut your pricing, but they can’t replicate the relationships you built when you were small enough to treat every customer like they were part of your team.

Key takeaways

• Your first 10 customers are worth exponentially more than customer #500 because they give you momentum and help you build.

• Raving fans give you references for customers and investors, market intelligence from competitors, and leeway to mess up when your product goes down or prices increase.

• The tactics that create raving fans aren’t scalable, but it builds company DNA and culture that can last forever, differentiating you from the competition.

• Not all early customers will become raving fans, but you’ll create a nucleus you can mobilize, leverage, and trust for years.

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FAQs

• How many customers should I treat this way? Start with your first 10. After that, you need to start thinking about scale, but the culture you build doing those things should persist as you grow.

• What if I can’t afford to give away free implementation help? The ROI from these customers who actually use and love your product far exceeds any service revenue. This is an investment in building advocates, references, and long-term customers who will buy from you again when they join a new company.

• When should I stop doing monthly CEO 1:1s? Let growth dictate the transition, no arbitrary timelines. I went from monthly to quarterly as we scaled, then eventually phased them out at a larger scale. But in the early days, that recurring time is critical.

• Isn’t this just good customer success? Yes, but it’s beyond that. You’re treating your first customers like employees when it comes to access, attention, and investment. Standard customer success doesn’t typically involve the CEO doing monthly calls. These tactics are deliberately excessive and not scalable.

You have an idea of a product you want to build, a problem you want to solve, and a customer you want to serve. You might have a basic MVP or a working prototype. Or maybe you haven’t written a single line of code yet.

Whatever the case, you’ve decided to start a company, and you’re staring at a huge milestone ahead: you need to find your first customers.

That period from zero to 10 customers is brutal. You’re starting from nothing. You’re trying to build momentum with no brand reputation and a very basic product, if anything at all.

As the CEO, you’re the first salesperson. Whether you’re an engineer, a marketing person, or a product person, your job is sales. Even if you’ve never done sales before, that’s your job now.

Of course, this won’t scale, but most of what you need to do at this stage is completely unscalable. And that’s ok. You just need a few early wins to get momentum.

In this article, I’m going to share six ways to find your first customers. One principle applies across everything: ask everyone. Every conversation should end with some version of ‘Do you know anyone who might be interested in what I’m building?’

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Table of contents

1. First, get comfortable asking for help

2. Reconnect with former employers

3. Leverage investor networks

4. Attend conferences where your buyers are

5. Make the plea on social media

6. Share your plans with friends, family, and everyone you know

7. Do cold outreach

First, get comfortable asking for help

This might be the hardest part. Most founders freeze when it comes time to tap their personal networks or reach out to a former colleague. They worry it seems desperate, unprofessional, or like they’re taking advantage of relationships.

In reality, your network wants to support you. They just don’t know how to help unless you tell them explicitly. Most people are honored when you ask them for advice or an introduction. It makes them feel valuable.

So before you try any of these six tactics, get comfortable with the idea that asking for help is part of the job.

Reconnect with former employers

This one is more common than you might think. Go to the person at your former company who’s in the job function you’re building for. Someone you worked with, someone you have a good relationship with.

Say something like, “Hey, we used to work together, and as you might know, I’m building a product that’s meant to make your job easier. I know from our time together at [company name] that we had these problems. Would you be willing to try it out?”

A lot of times, especially depending on the size of the company and when you were there, the team manager or the CEO will want to support you. There’s goodwill built in from your time there, and they will want to help you out.

Tip: Even if they don’t think it’s a good fit for their team, ask whether there’s anyone else at the company or in their network who might be a better fit. Make it as easy as possible for them to make the intro by offering to write it yourself or to write an email they can forward.

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Leverage investor networks

Whether you have investors or not, if you’re building a venture-backed company, you’re probably meeting with investors at some level. And many times, an investor will finish a call or meeting with something like, “Let me know if there’s ever anything else I can help you with.”

We often forget that this is actually an opportunity. Maybe we don’t see it as a real path to acquiring customers, or perhaps we’re just afraid to make an ask at this point. Whatever the reason, we let it pass.

Don’t let it pass.

Instead, be specific about your ideal customer profile so they can make targeted introductions that actually make sense. Will this get you 20 customers? No. Will every introduction turn into a customer? No. But you only need it to work once or twice.

You can also look up people who angel invest in your space. Use Crunchbase, AngelList, and other tools to find people who are actively investing in your specific area. Reach out to them and ask them for connections.

Tip: Be hyper-specific about your ideal customer profile so they can make targeted introductions that actually make sense. Again, make it easy on them: review their portfolio companies and tell them which ones fit your ICP best. Don’t make them do that work.

Attend conferences where your buyers are

You don’t need to speak at the conference. You don’t even need a booth. You just need to attend. Go to conferences where you know your target buyer will be.

For me, in the early days of BetterCloud, when we were targeting Google customers, I went to every Google I.O. event. It was hard to get tickets, but we did everything we could to get there. And then I went to every event Google Cloud (then called Google Enterprise) was hosting. I was attending small, happy-hour-style events with hyper-focused audiences where my target customers were.

I actually got several customers this way. They were all there, and they were all open to having a conversation over a couple of drinks. It wasn’t me at a booth. It was me literally seeking them out and saying, “Hey, I see you’re a customer of Google. We service Google customers. Can we have a conversation?”

This is expensive, especially when you don’t have any customers yet. Flights, hotels, meals. That stuff adds up quickly. But when you’re just starting out, and you walk away from a trip from New York to San Francisco with one customer, that’s major progress.

If you’re a company doing $10 million in revenue and you come back with one customer, that’s probably a failure. But in the early days? One is a success.

Tip: Don’t skip unstructured events (happy hours, hallway conversations, etc). This is where people are most relaxed and open to conversations. You might be tired after a long day of sessions, but you need to prioritize these moments to make real connections.

Share what you’re building on social media

Write a LinkedIn post announcing you’ve gone out on your own and you’re building something exciting. Tell your audience who you’re building for, and that you’d love to connect with these folks if they’re interested in helping shape the future of the area you’re focused on.

Is this going to get you a ton of customers? No. But again, you only need it to work once or twice.

Some people will respond to this because they like you personally and have worked with you before. Others will respond because they’re genuinely interested in what the next cool thing is. Either way, you’ll see people raise their hands and want to support you.

Don’t stop there, though. Building a presence on LinkedIn as a CEO has become a key part of SaaS go-to-market and marketing. The more you post about what you’re building, the more visible you become to your target audience, and the easier it is for people to find you when they need what you solve.

Tip: Don’t just post on LinkedIn. Share updates on Instagram, Facebook, wherever your personal network is. Your friends and family might know someone in your target role. Cast a wider net than you think you need to. A lot of people love learning about new products hitting the market, and they want to be early adopters.

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Share your plans with friends, family, and everyone you know

You have to start somewhere. My first Vocalocity customer was my uncle, who ran an office. He needed a phone system, and that’s exactly what we sold. My second customer was my best friend from college. There’s no shame in this. Use every connection you have because that’s what it takes at this stage.

Make sure every person you come across knows what you’re building. Every conversation, whether it’s personal or professional, should end with some version of “Do you know anyone who could be a good design partner for what I’m building?”

Your success rate will be minuscule, but putting in the work isn’t an option at this point. At the very least, it’s brand awareness, and the best-case scenario is you get a customer. One win at this stage is a huge step forward.

Human beings want to be helpful and seen as experts. When you ask for help or an introduction, you’re giving them that opportunity.

Tip: Don’t be shy about this. Your personal network wants to support you. Even if it feels awkward, push through. You’ll be surprised by the results.

Do cold outreach

This one’s hard because you’re doing this with no reputation. But with the right message, it works. The key is remembering you’re not selling. You’re asking for advice, feedback, and suggestions. I’ve done this, and I’ve seen it work.

It can be as simple as, “Hey, you’re a CEO, I’m a CEO, I’m building this company, and I’m also based in New York,” or “I’m also in IT,” or whatever the connection point is, “and I would love to just get your take on what I’m building.”

A lot of times, I get these messages, and I’ll get on a call and tell them it’s a good idea. And then they’ll say, “Hey, I see you advise companies A, B, and C. Would it be possible for you to make introductions to those people for them to test my product?”

That’s how it works. You’re asking for 15 minutes of their time to get feedback, see if they are interested in the product and/or then you’re making the ask for introductions.

Tip: Keep the initial ask small. A few minutes of feedback is easier to get than a full demo or sales call.

This gets you customers, but it doesn’t guarantee success

These six tactics can get you in front of your first 10 customers, and while none of them scale, that’s ok. The goal is to get your foot in the door and build momentum.

But getting in the door doesn’t mean you’ll keep them. You still have to deliver a must-have product. To retain customers long-term, you need something that truly solves a painful problem, and then you need to do everything you can to deliver value over and over again.

In our next article, we’ll share tips for turning your first 10 customers into raving fans. Subscribe here to get it in your inbox.

Key takeaways

• As CEO, you’re the first salesperson. Regardless of your background, a big part of your job at this stage is sales.

• Everything you do to find your first 10 customers will be completely unscalable at this point. But one customer is a significant step forward when you’re at zero.

• Former employers, investors, conferences, social media, personal networks, and cold outreach are all viable paths to your first customers.

• Getting customers in the door doesn’t guarantee success. You still need to deliver a must-have product that solves a painful problem.

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FAQs

• Do I need to hire a salesperson to get customers? No. Especially early on. As the CEO or cofounder, you should be the one selling the product in the early stages. Not only is this more economical, but you’ll also learn more about your ideal customer, your market, and your product the more you talk to prospective customers.

• Should I incentivize the early customers who help me build? That depends on your product and business model. Many founders offer early customers steep discounts or even free access in exchange for feedback and a case study. The goal at this stage is learning and validation, not revenue.

• What’s the biggest mistake founders make when seeking their first customers? Waiting for customers to come to them. You can’t sit back and hope people will find you. You have to put yourself out there, even if it’s outside of your comfort zone.

I was the Senior Tech Creator Manager at LinkedIn. For over three years, I worked with Fortune 500 tech CEOs, VCs, and founders, advising them on how to drive their goals (land clients, raise capital, and attract talent) using LinkedIn posts.

I see content as a Trojan Horse. Posts that educate, help, and entertain lead to more sales, better hires, and connections to investors. A typical CEO, whose resources are finite, should invest at least some of their content into creating content that supports their next business milestone.

I’ll start by demystifying the LinkedIn algorithm, as it’s the first thing people always ask me about. I’ve read countless theories about what a post needs to break through, and the vast majority are wrong. Really wrong. I’ll start by answering the top questions I get (such as: “can I share a link in a post?”) because if the few thousand people I’ve trained to succeed at LinkedIn have these questions, you probably do too.”

I’ll give you answers as a LinkedIn insider who was in the belly of the beast.

But here is the reality: most of the answers to top algorithm questions make only a marginal difference. Getting answers to the most common questions about formatting, timing, hashtags etc. feels good. It might be an easy win, but it doesn’t do much good if your goal is to drive business.

So what is the LinkedIn hack that actually works? Understanding why LinkedIn’s one billion users are on the platform and what they’re looking to solve. Because then you can give them the advice they’re already looking for. This turns you from another CEO who appears in their feed into a trusted advisor they want to do business with.

Table of Contents

1. Top LinkedIn algorithm questions

2. What actually works on LinkedIn

3. Two posts that LinkedIn audiences love

4. Succeed by helping your audience make progress

5. An example of practical, actionable guidance

6. Industry insider example

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Top LinkedIn algorithm questions

These are the questions I get at the start of every workshop and strategy meeting. I hope my answers help orient you.

Of course, there are exceptions, but the advice here applies to the vast majority of founders and CEOs. Keep in mind that this is an article, not a 1:1 consulting session, so as with any advice, use your judgment on how it applies to your unique situation.

When should I post?

When is your target audience on LinkedIn? For most people, the answer is Monday to Friday, during working hours. If that’s you, aim to post bright and early (around 8am or 9am), to give your post the best chance of being seen by as many people as possible..

How often should I post?

Try to post at least once a week to build traction. And I suggest that a typical founder aims for three times a week to really create momentum — not just with the algorithm, but with your audience.

I don’t recommend posting more than once per day. Sometimes you can’t avoid it, though. For example, if your company has several time-sensitive announcements to share, you might want to post more than once per day.

How do I increase engagement?

LinkedIn audiences love seeing responses to comments, even if they aren’t their own. It feels like a reward, a behind-the-scenes, off-the-cuff moment. If you engage with comments, more of your audience will engage with you too.

Like a writer engaging with fans, this turns a post into a conversation between peers, and it feels like a reward. Again, this is less about the algorithm and more about human behavior.

Rather than just saying “thank you!” to everyone, I recommend replying to a handful of comments with thoughtful answers that extend the conversation or introduce a new angle.

Should I use hashtags?

Hashtags aren’t a major discovery mechanism on LinkedIn, so they’re not necessary for success. If you want to use hashtags, I recommend using no more than three and putting them at the end of the post.

What’s the best way to tag people?

You should tag people if they directly play a part in the story you’re telling. Tags should be used to connect readers to the companies and professionals that are core to your message. Audiences are smart, and if you’re tagging as a growth hack, it can look spammy.

Should I use font generators to make my post more visually interesting?

Using custom formatting that isn’t available on LinkedIn, like bolded or italicized text, can make your post harder to read for people using screen readers or accessibility tools. I highly recommend sticking to the native formatting tools on LinkedIn.

Focus on writing strong opening lines for each paragraph. Make it clear where you’re going and what each section is about. This helps you stand out because it makes your writing easy to follow. Special fonts can’t (and don’t) compensate for weak writing or unclear thinking.

Should I share the link inside a post or in the comments?

The reason posts that link to a blog, podcast, or other external content flop is that people click the link and run. It’s a lot to ask someone who’s come onto LinkedIn to leave LinkedIn, so you have to give them an incentive.

To do well, posts with links have to work as standalone posts. They need to be as compelling as a post that doesn’t include any links. So the post itself should be valuable: 3-4 paragraphs, clear takeaways, and either a summary of what you’re linking to, or your reaction to it.

In short, you can add the link in the post. Just make sure the post earns the click. If you want someone to go off-platform, make it worth their while.

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What actually works on LinkedIn

We’ve covered the most common algorithm questions. But none of that guarantees success. Hashtags, timing, and formatting are just accessories.

It’s the difference between the color of a car and the motor. You can spend hours debating what shade of Prius to buy, but the color doesn’t make the car drive; it’s just packaging.

So what’s the motor, the key to a successful LinkedIn post?

Doing LinkedIn well is about understanding how human beings think. What they care about. What makes them want to read a post is the same instinct that makes us want to pick up a book at the airport or watch a documentary.

Adam Grant is successful on LinkedIn not because of the number of hashtags he uses, or whether the link is shared in the post or in the comments. It’s because he fundamentally understands audience psychology — what makes someone stop and read.

People read Adam Grant for the same reason they read someone like Barbara Corcoran: there’s something in it for them. Thanks to Grant or Corcoran, they learn how to work more effectively or understand what’s happening in their industry. In the case of Grant, that’s often a practical suggestion for working better or an observation of a shift happening in the workplace.

LinkedIn users are on the platform for one reason: to progress professionally. That might mean landing a new customer, raising capital, hiring talent, or building industry relationships. People who don’t already know you will only read your content if it helps them make better business decisions or understand where their industry is going.

By contrast, posts fail when they’re vague musings instead of tools. When it comes to attracting new readers or strangers on the internet (people who could become customers, employees, or investors), they stop scrolling only if the post offers clear value to them. And on LinkedIn, that value usually falls into one of two categories.

Two types of posts LinkedIn audiences love

The posts that do best on LinkedIn do one of two things: they help the audience work more effectively or better understand their industry.

For example, Grant might share a study about burnout and then distill it into one clear behavior managers can change tomorrow. Corcoran might take a headline about the housing market and explain what it actually means for buyers and sellers right now.

Practical, actionable guidance

The first type gives audiences practical, actionable guidance they can apply immediately to do their jobs better or advance their careers faster. This type of content addresses those challenges directly.

For example, if you sell an enterprise HR product and your customer is HR professionals, the questions that should guide your post ideas are simple: What have your clients asked you or your team for help with in the last few months? What are your clients most concerned about right now? What are they actively trying to solve? It’s less about what performs well on LinkedIn and more about what you can share that will make the lives of your audience easier.

To create posts that give practical guidance, ask yourself:

• What mistake do I see my customers making repeatedly?

• What process could I help them improve by 10%?

• What question am I answering in sales calls every week?

Name an industry trend or shift

The second type of successful post names an industry trend or shift and, most importantly, gives audiences ideas for how to respond.

People come to LinkedIn for guidance, not just for the news or the facts. They’re used to going to a journalist for something that feels like reporting. They come to you because you’ve been in the trenches. They want to hear: here’s this thing that’s happening, and here’s something you could do about it.

To create posts that expand on industry trends, ask yourself:

• What regulation or shift will affect my customers in the next 6 months?

• What’s everyone talking about at conferences that my audience might have missed?

• What change am I seeing that others haven’t connected the dots on yet?

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Succeed by helping your audience make progress

Whether you’re offering practical guidance or naming a shift in your industry, the principle is the same — people will tune into your posts if you can help them make progress. Audiences value actionable, tactical advice and insights they can use. The algorithm simply scales that behavior, distributing content they’re already primed to be looking for.

But what do you do once you’ve found your topic? You over-invest in your opening because everything above “see more” is your shop window, and you need to make that storefront as inviting and interesting as possible.

Your opening is make-or-break

Before we talk openings, let’s be clear: Without actionable, tactical insights that help your audience progress in their career, nothing else matters. You can’t hack your way to a good post with hashtags and linebreaks. If you don’t know what your audience wants, it doesn’t matter how you package your post.

But once you have a nugget to build your post around, your opening is the best investment of your time.

Think of the two lines above “see more” like a shop window. You can have the best products inside, but if your window doesn’t make people want to step in, they’ll walk right past.

I constantly see founders post excellent content that gets ignored because the opening doesn’t signal what’s inside. They bury the insight three paragraphs down. They make their audience work to figure out what the post is about. Or they try to create mystery or tension when really, we just want you to tell us what you’re going to tell us.

This might seem counterintuitive, but let’s think about the LinkedIn user. They aren’t sitting at a desk with a cup of tea, ready to read. They’re scrolling quickly between meetings, in line at Starbucks, or they’re on their commute. You have seconds,not minutes, to signal “this post is for you.” And your opening is how you entice them to stop scrolling. If someone doesn’t click “see more” in those first two lines, they never will.

At school, we learned to build to a conclusion and save our best point for last. But for a busy LinkedIn audience, you have to flip that entire structure. Your best point goes first. People want to know what they’re going to get if they click “see more”, they want to know it’s worth their time. So don’t hold back. Invest in that opening.

A few years ago, there was a fad for openings that attempted to manufacture tension or mystery. The novelty has worn off because people know the formula now. When you lead with mystery, you’re asking busy strangers on the internet to take a leap of faith. But keep in mind that it’s tough to get someone into a store with an empty window or no signage.

How to write a strong opening

I recommend working on the opening once the rest of the post is done. When you’ve finished your post, go back to the opening and ask yourself: Is my best point here? If your strongest point is halfway through the post, move it to the top. Don’t save it for later. You won’t get a “later” if people don’t click “see more.”

Here are a few other tests to run on your opening:

Does it signal who this is for? Name-check your audience. “If you’re raising a Series A...” or “For B2B marketers struggling with...” makes it easy for the right people to self-select.

Does it tell them what they’ll get? Be specific. Instead of “Here’s what I learned about hiring,” try “Here’s how to screen engineering candidates in 15 minutes instead of an hour.” Instead of “Thoughts on fundraising,” write “Here’s how to decide whether to take that term sheet or keep looking for investment.” Or instead of a broad post about pricing strategy, get specific: “Here’s how to price your product when you have no comparable competitors.” People like posts that solve problems rather than philosophical musings. The more your post maps onto your audience’s real, daily concerns, the better.

Would you click “see more” on this? Read your opening as if you’re scrolling quickly. Be honest. If you wouldn’t stop, rewrite it.

An example of practical, actionable guidance

We’re going to dissect a couple of LinkedIn posts by our very own David Politis.

David published a post about hiring for grit that demonstrates exactly what a strong “Help me work better” post looks like.

Here’s the opening:

“I’ve spent my entire career, almost 20 years now, at startups. Throughout that time, I’ve hired hundreds, if not thousands, of people. The #1 skill/attribute that I’m always looking for is grit.”

Notice what’s working here. Within two lines (everything visible above “see more”), you know exactly what this post is about and who it’s for. If you’re a founder or hiring manager trying to build a team, you immediately understand this post has something for you. David signals his authority (20 years, hundreds of hires) and names the specific insight (grit is #1). You don’t have to guess whether clicking “see more” will be worth your time.

The rest of the post delivers on that promise. David doesn’t just tell you grit matters – he defines what grit actually means in a startup context (determination, resilience, thriving in wartime), explains why it’s critical (startups face constant adversity and change), and gives you a framework for thinking about hiring in the current environment.

This post helps the audience work more effectively. It solves a real problem founders face: how to evaluate candidates. It’s specific, tactical, and rooted in David’s direct experience. That’s why it works.

Industry insider example

Here’s another post by David using the Industry Insider strategy.

Here’s his opening:

“Historically, there are two departments that have operated in the background at almost every organization. But they’re critical to every company’s success, especially in today’s world. Which two departments am I talking about? IT and Security.”

This opening immediately signals a shift: departments that used to be in the background need to move to the foreground. If you’re a founder, executive, or anyone responsible for IT/Security, you know this post is relevant to you.

The post then explains the trend: IT and Security can’t operate effectively from the shadows anymore. Every company relies on technology, every company faces cybersecurity risk, and these teams need visibility and buy-in to do their jobs.

But here’s what makes this an effective industry insider post: it doesn’t stop at diagnosis. The post gives you a clear roadmap for what to do about it:

• Get executive support and recognition (with specific examples: CEO emails, executives modeling behavior)

• Embed IT and Security in employee touchpoints from onboarding through exit

• Create regular visibility through all-hands meetings and company communications

• Celebrate wins and show impact with data (90% reduction in phishing clickthrough, faster sales outreach)

• Tailor messaging to executives and boards around risk reduction and productivity gains

He’s following the formula to a tee, telling us what’s changing in your industry and what to do about it. The audience walks away with both understanding and action steps. That’s what makes an Industry Insider post valuable.

Focus on your audience

Stop optimizing for the algorithm and stay focused on your audience. If you can help the people you want to do business with make better decisions, move faster, or understand something they didn’t before, they’ll come back. And when they’re ready to hire, invest, or buy, you’ll be the first person they think of. That’s the whole game.

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Key takeaways

• Hacking the LinkedIn algorithm isn’t the growth engine; understanding audience psychology is. Timing, hashtags, and formatting make marginal differences. What matters is understanding why people are on LinkedIn: to make progress in their careers.

• Content should serve your business goals. Great posts act as a Trojan Horse. They educate or clarify. That leads to sales, hires, and investor conversations.

• Two types of posts consistently drive results: The first is practical, actionable guidance your audience can apply immediately. The second is industry shifts explained, plus what to do about them. If a post doesn’t help someone work better or think smarter about their industry, it won’t travel.

• Posts must stand alone, even with a link. If you want someone to leave LinkedIn, earn the click. Deliver value in the post itself first.

• Engagement is conversation, not hacks. Thoughtful replies to comments build momentum. The algorithm scales the value; it doesn’t create it.

FAQs

What actually drives business on LinkedIn?

Posts that help your audience make progress. That usually means sharing practical guidance they can apply immediately or naming an industry shift and explaining how to respond.

Does the LinkedIn algorithm penalize posts with links?
No. Posts with links flop when they don’t deliver value on their own. The post should be compelling even if no one clicks.

How often should founders post?

At least once per week. Three times per week builds real momentum. Avoid posting more than once per day if you can.

What’s the real LinkedIn “hack”?

Understand what your audience is trying to solve, and help them solve it. Everything else is packaging.

It’s the middle of March, not even a full quarter into the year, and I know exactly what’s happening at your company: That plan you laid out and rallied behind in January has gone by the wayside.

Maybe a customer asked about a feature you haven’t prioritized, or an investor floated an idea that got in your head. Maybe you had an epiphany at 11pm that felt too good to ignore, a competitor raised a massive round and announced a free product that competes directly with yours, or a marketing opportunity came up that wasn’t in the original plan.

This is all fine. Ideas are good. They drive innovation. And it’s ok to react to what’s happening with customers, competitors, and markets. The problem is, those ideas are getting layered on top of a plan that was already way too optimistic. And now you have all these new ideas you want to chase, but you’re not sure if they’re the right path.

If you keep stacking these ideas onto your plate without reprioritizing, you’re setting yourself (and your team) up for a rough Q2 and the rest of the year.

This happens every year at almost every company. And there’s a way to handle it, but it requires some discipline before Q2 starts.

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Table of contents

1. Why CEOs lose focus

2. What happens when you don’t stay focused

3. How to actually stay focused (and maintain momentum)

Why CEOs lose focus

Our eyes are bigger than our stomachs. Every company overestimates what it can achieve in a given year. I recently spoke with Amish Jani, and he shared a quote that really resonated:

“Most companies don’t die of starvation; it’s indigestion, too many different things at once.”

This doesn’t mean you’re flawed — it’s just optimism. When you’re planning in December for things that won’t happen until September, it’s easy to think your future self will be able to handle it. “Of course, we can do that. Add it to the list.”

And when new ideas start coming in on top of that already-stretched plan, your team doesn’t know what to work on. And you’re not sure either.

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What happens when you don’t stay focused

The most immediate casualty is clarity. Your team starts asking (out loud or just to themselves) what they should actually be working on. The things you agreed on in January, or the new things you just gave them?

Take hiring, for example. You planned to bring on 10 people. But based on new initiatives, you’ve now added five more to the list, and the roles (and the priority of those roles) have changed. Right or wrong, your team wasn’t prepared to hire 15 people. And the people who were waiting for those first 10 to onboard? Their plans just got pushed back.

That trickle-down effect hits every department. Say a customer call gets you excited about a new feature, and you tell the product manager to shift gears and start on it right away.

But the product marketing team was already heads-down on the launch campaign for the original initiative before you redirected them. And sales already promised the original feature to prospects (even though they shouldn’t have; they heard about it at the last company meeting and ran with it).

Now you’ve got a ripple effect across three teams, and nobody’s sure what they’re supposed to be doing (or saying) anymore.

The sequencing that makes cross-functional teams actually function falls apart when you start pulling threads mid-cycle, and nothing gets finished.

You also lose your ability to forecast. When the plan is constantly shifting, you can’t get a clear read on where the business is actually headed. The worst part is your team sees this in you, and it instills a lack of confidence.

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I’ve lived this many times. Early on, I used to change the product roadmap based on the most recent customer conversation. My team would be in the middle of a multi-sprint project, and I’d come in with something new. Six months later, I’d be frustrated. “Why didn’t we ship feature A?” And they’d tell me: “Because you asked us to stop and build feature B.”

It’s trade-offs. And we eventually had to make it a rule. We said there would be no changes to the roadmap for at least three sprints. It started as one sprint, then became three as I learned to trust the process. But that rule shouldn’t have been necessary. The discipline should have been there from the start.

When you pull people off something mid-stream, they lose time and momentum. This applies to every function, not just the product and engineering teams. There’s a ramp-up cost every time someone has to reorient to a new priority. Context switching is expensive. And when things do eventually ship, the quality suffers because the job was rushed.

How to actually stay focused (and maintain momentum)

The answer is to build a process for handling new ideas and competing priorities. Here’s how.

1. Take it to your leadership team

When something new comes up, don’t just push it down into the organization. Bring it to your leadership team first. Put it up against everything already on the list and reprioritize together. That conversation acts like a filter, and it’s where you’ll get clarity on what to do next. Your team will also feel valued, fostering a culture of collaboration rather than top-down decision-making.

2. If you add something, remove something

Adopt this rule: If something new comes in, something of equal or greater size must come out or move down. No exceptions. The plan doesn’t have unlimited capacity, and pretending it does is how you end up with a team that’s stretched across too many things and finishing none of them.

And let’s be honest: the original plan was probably already too overloaded and unrealistic. This kind of chronic context-switching is one of the fastest paths to burning out your team and building resentment for the company you built.

3. Communicate why things changed

Change is okay. Given the speed at which businesses move today, some level of change is inevitable. The problem is when those shifts don’t get communicated.

As CEO, you’re the hub. You know everything. You were on the call with the customer, you heard the investor’s idea, and you had the epiphany. But it’s easy to forget that nobody else has that context. They don’t know what changed, and they definitely don’t know why.

When the plan changes, your team deserves to know why. Not just what shifted, but what you learned, what triggered the change, and what the impact will be. And if this decision pulled someone out of something they were deep into, or redirected their work midstream, acknowledge it.

You don’t need to apologize, but recognizing that it happened and appreciating their flexibility goes a long way. That context is what separates a team that trusts leadership from one that’s constantly second-guessing the direction.

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4. Plan quarterly, not annually

I used to plan the entire year upfront and feel great about it. Someone once asked me how often I revisited those goals. I told them, “Once a year, at planning.” They looked at me like I was crazy.

“You need to get together every quarter as a leadership team,” they said. “The world moves too fast for anything else”.

They were right. Things are going to change. That’s just reality. Maybe 15-25% of your plan shifts each quarter. That’s okay. The goal isn’t a perfect plan. The goal is a current one.

But once you’ve reset for the quarter, lock it in. Don’t change things mid-quarter if you can help it. Let your team build momentum, finish what they started, and ship something they’re proud of.

Make the choice to focus before Q2 starts

Every CEO I know has lived some version of this. The year starts with a solid plan, new ideas come in, things get layered on, and by the time Q2 arrives, you’re wondering why nothing got finished.

It doesn’t have to go that way. But the window to course-correct is right now, before Q2 starts. Get your leadership team together. Put everything on the table: the original plan, and everything that’s been added since January. Reprioritize it together, communicate the changes clearly, and then lock it in for the quarter.

That’s it. It’s not complicated. But it requires discipline to actually do it.

At each company I’ve been a part of, I can name the top 10-15 people who made it successful.

You probably can too. Whether you’ve got 25 employees or 500, there’s a small group carrying a disproportionate amount of weight. They’re the ones whose names come up in every important meeting. The ones customers know and love working with. The problem solvers everyone goes to when something critical happens.

I was introduced to Price’s Law last year during a podcast interview with Alan Masareck. It says that the square root of people in any group working on a project is responsible for 50% of the results. At 100 people, that’s 10 people. At 1,000, it’s about 32.

Think about that. A company with 1,000 people, and 32 are really the ones driving the business forward.

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But here’s what makes these people truly irreplaceable: they don’t just do their own work exceptionally well. They make everyone around them better. They lift up their teams. They solve problems before they become crises, they drive innovation, and they attract other great people to work with you. When they walk into a room, the energy shifts. And when they leave, you lose all the momentum they brought with them.

And if you lose one of them, you’re not replacing them with one person. You’re looking at multiple hires, multiple rounds of interviews, and months of ramp time, and you still might not fill the gap they left. The likelihood of finding another person at their level who fits the way they did and will have the same impact is very low.

So how do you make sure these top performers never have a reason to leave?

This article covers how to identify your best employees, and the specific tactics I’ve used to retain and grow them: recognition that matters, one-on-one time that strengthens relationships, removing friction fast, creating custom career paths, and compensating proactively.

Table of contents

1. Identify your top performers

2. Recognize them

3. Meet with them one-on-one

4. Remove friction

5. Give them opportunities to accomplish their goals

6. Promote and compensate them

7. Your job is to give them no reason to look elsewhere

Identify your top performers

Here are the fastest ways to identify the people carrying the most weight at your company:

Trust your gut. You probably already know the top five or 10 people at your company off the top of your head. Their names come up repeatedly. They’re constantly raising their hands for the hard initiatives, the biggest projects, and the things no one else wants to touch. And they crush all of those projects.

Ask your leaders. Go to every department head and ask them who they would hire first if they were starting their own company. These are the ones they couldn’t do without. The ones they wish everyone else modeled themselves after. You’ll see patterns emerge quickly.

Look at your review process. If you’re doing performance reviews, look at who got the highest ratings. But don’t just look at the score. Look at the comments. Who’s getting called out for impact beyond their role?

Check collaboration tools. Go through Slack, Teams, whatever system you use, and look for whose names get called out repeatedly. Who are people thanking? Who are they tagging when they need help? Who’s being publicly recognized by their peers?

Through one or more of these methods, you’ll identify your best people. And once you do, your job is to remove obstacles so they can do their best work. You need to show them they’re valued, and give them a clear path to achieve their goals and grow. Get this right, and they’ll have no reason to look elsewhere.

It starts with recognition.

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Recognize your top talent

Recognition is the easiest thing you can do, and it’s often more meaningful than money. There are different ways to recognize these people.

Public recognition

At BetterCloud, we gave out “BetterClouder of the Year” awards at our annual company kickoff. We’d give people custom Beats by Dre headphones in bold colors so that when they wore them in the office or on Zoom calls, everyone knew they’d won. It was scarce, it was visible, and important. When someone walked around the office with those headphones, everyone knew they’d won. People would tell me, “By the time I leave this company, I’m getting that award.”

But recognition doesn’t have to be that formal. Many companies recognize their top talent at the end of their monthly all-hands meetings. A Slack shoutout calling out someone for a specific win works. Showing up at an AE’s desk with a bottle of wine after they closed a huge deal also works.

The point is, the effort matters more than the gesture itself.

Recognition should also flow from multiple levels. I’d recognize people publicly, but I’d also urge managers to recognize their team members. When recognition becomes part of your culture, not just something the CEO does, it compounds.

Personal recognition

Find out what your top performers actually love and reward them with that when they go above and beyond. If they’re a big traveler, get them a gift card for their favorite airline. If they’re a foodie and you hear them talking about some new restaurant, make them a reservation and pay for the meal. It shows you’re paying attention.

Written recognition

Especially at the end of the year, end of a quarter, or after an important sprint or product launch, take the time to write them a note explaining why you appreciate them. CC their manager. It takes five minutes, and they’ll forward that email to their parents, significant others, etc and save it forever.

Recognition during reviews

During performance reviews, don’t just tell someone they got a five out of five. Let them know they’re in rarified air and that only a small percentage of the company got that rating.

Before you even deliver the ratings, review the top-rated people at an executive team meeting to ensure alignment. Then, when the manager delivers the rating, they should tell the person that their performance was discussed and agreed upon by the entire leadership team. That carries a ton of weight.

Recognition doesn’t cost anything, but it means everything to the people who are carrying your company.

Meet with them one-on-one

If you want to retain your top talent, you need to invest time with them. I make it a point to meet one-on-one with the top 5% of people at least once a year. This creates a special relationship and signals that they’re valued differently.

But it shouldn’t just be the CEO. The head of people and their direct manager should also be spending extra time with them. They should be closely attuned to their impact and understand their career objectives. When multiple leaders invest in someone, it reinforces how important they are.

In these meetings, I ask three questions:

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Question 1: “What’s the number one thing that motivates you?”

The answers vary widely. One person told me their title was most motivating. They wanted their LinkedIn to show their career trajectory. Engineers often say solving the most complex problems motivates them. Someone said learning. Another said they’re motivated when someone else on their team is successful. Salespeople are usually motivated by making the most money possible or owning a flagship account.

Then I ask a follow-up: Why does that motivate you? This is actually where you learn the most. You’ll begin to understand events from early in their lives or careers that shaped who they are today. Bottom line: You can’t motivate people if you don’t know what drives them, and you shouldn’t assume anything.

Question 2: “What’s causing the most friction in your work today?”

Top performers often work around friction rather than complain about it. But when you ask directly, you’ll get clear answers. You’ll hear about the daily report they have to create that no one reads. Or the red tape they have to jump through that’s slowing them down.

This question uncovers what’s quietly frustrating your best people.

Question 3: “If you were me, the CEO, what’s the one thing you’d do to grow this company?”

People know the answers better than you think. They just aren’t volunteering them.

One salesperson had a 10-page document ready on an entire module that customers were asking for. An engineer identified a $20k tool that would make every engineer 5% more productive. These are real opportunities sitting right in front of you.

The insights from these three questions are gold, but only if you act on them.

Remove the friction

Removing friction is easier than you think, but friction can cause more frustration and damage than you can imagine.

Average performers encounter red tape and give up. They lose steam and either aren’t sure how to move forward or just decide not to.

Meanwhile, top performers find ways to work around bureaucracy. They do whatever it takes to get their job done. And as CEOs, we see them succeeding despite the friction and think everything is fine.

But every time they work around broken processes, they’re frustrated. Every time they have to navigate red tape that shouldn’t exist, it wears them down. Our job, as CEO, is to seek out those rough edges and smooth them down.

When you learn what’s slowing down your top performers, act quickly. Don’t put it on a roadmap for next quarter. Don’t wait for budget approval. Just solve it.

Examples of friction I’ve removed:

• A support rep was frustrated by a seven-step approval process just to add a free service for a customer. It made no sense and was slowing her down. We simplified it to two steps.

• One engineer mentioned he wanted a standing desk to work more comfortably. I got it for him the following week. It cost a few hundred dollars and made him more comfortable for the thousands of hours he’d spend at that desk.

• Another engineer needed four monitors and a custom rig to accommodate the screen space his work required. We didn’t ask questions or make him justify it. We just set him up with what he needed to do his best work.

• Someone needed a quiet room to focus because the open office was killing their productivity. We converted an unused conference room into a dark, peaceful space. Problem solved.

• Someone had to complete a daily form that their manager never reviewed. It was pure bureaucracy with no value. We killed the form entirely.

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These aren’t expensive fixes. They’re just things no one prioritized because the best performers worked around them rather than complained.

However, friction can sometimes be caused by people. So part of reducing friction also means removing people who slow down your best employees. The best people want to work with the best people, and bad teammates drain your top performers faster than any broken process.

Removing friction for your top employees comes with significant returns. Every minute they’re not fighting bureaucracy, not dealing with bad teammates, or not working in an uncomfortable environment is a minute they’re moving your company forward. At the same time, they’ll see that you’ve taken the initiative to help them do their job better and that you want them to be as successful as possible. That’s rare, and therefore greatly appreciated when it happens.

Give them opportunities to accomplish their goals

Once you know what motivates your top employees, map their career paths to match that motivation. This isn’t the path you think they should want, or the default path the majority of your employees take. You need to design a custom career path that they actually want.

The biggest mistake I see is assuming every top performer wants to be a manager. They don’t. Some of your best individual contributors want to stay individual contributors. Pushing those employees into management doesn’t keep them around, it frustrates them and creates a mediocre manager.

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Find out what they want to accomplish, and help them get there.

Examples of custom career paths I’ve created:

• One engineer wanted to learn and see different parts of the platform. We created a rotation program for him that would allow him to work with different teams and projects over 18 months.

• A support person wanted to go to business school to become a product manager. Instead of business school, we had them start meeting with our head of product every month, we gave them small projects, and 14 months later, they became a product manager.

• An engineer wanted to stay an IC but have more impact. We created a senior IC track with compensation and recognition that aligned with management levels.

• Someone was motivated by visa sponsorship and a path to citizenship. We helped them get their green card. It cost us legal fees, but it bought years of loyalty.

• A salesperson wanted to make $300k a year. I sat down with them and coached them through exactly what they needed to do to become an enterprise rep who could hit that number.

• Someone in a director-level position wanted to improve their executive presence. We identified opportunities for them to present to our C-level executives, had them host sessions at our customer conference, and helped secure speaking engagements at third-party events.

Some of these opportunities happen overnight. Others take years. But when you show someone the path, they’ll work twice as hard to stay twice as long because they can see where they’re going.

Promote and compensate them

While compensation matters, it’s often not the primary motivator for top talent. But it’s still really important.

Top performers should never have to ask for a raise or promotion. If they’re asking, you’ve already failed. You need to be proactive.

Pay them for the trajectory they’re on, not just their current performance. Remember, these are outliers. Don’t treat them like standard employees with standard compensation plans.

Tips for compensating top performers

• Give raises twice a year, rather than once, if their performance warrants it. Don’t wait for the annual cycle if they’re crushing it.

• Use spot bonuses for truly above-and-beyond work. When someone goes beyond what you expected, reward them immediately, not six months later during review season.

• Promote them ahead of schedule if they’re already performing at the next level. If they’re doing director-level work with a manager title, fix it now.

• Don’t let structure stop you from compensating correctly. The rules you think exist are probably just habits, not requirements, especially when it comes to your best employees.

• Give meaningful equity stakes. If they’re helping build something valuable, they should own a piece of it.

The objection I hear most often: “What if others find out?” My answer: If someone truly believes they’re performing at the same level as your top talent, they should talk to you. But outliers are unique by definition. Not everyone deserves the same compensation. And if you’ve truly identified the true top performers, everyone else at the company already knows they’re the best.

Compensation communicates thanks. It represents impact. But remember, if you’ve done everything else right (removed friction, given them recognition, invested time with them, shown them a clear path), compensation becomes the cherry on top, not the only thing keeping them around.

Your job is to make sure they don’t have a single reason to look elsewhere

Employee retention is one thing, but retaining your best people is an entirely different motion. It comes down to ensuring they have four things: minimal friction in their work, a sense of appreciation, meaningful compensation, and a clear growth path. And executing on that requires some out-of-the-box thinking.

When you get this right, you enable your best people to run through walls for your company. And every minute you spend with your top talent yields multiple times the ROI of time spent elsewhere. But there’s also a residual effect: When others see how you treat your top performers, they’re more driven to perform like them.

Your job as CEO isn’t to treat everyone the same. It’s to recognize that your top performers carry disproportionate weight and to ensure they have no reason to look elsewhere. Because losing them means losing their output, their problem-solving skills, the way they lift up everyone around them, and all the momentum they bring to your company.

Make it so they never want to leave.

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Key takeaways

• Your top performers carry disproportionate weight and also motivate others to perform their best.

• Identify top performers by asking leaders for their must-keep people, reviewing top ratings, trusting your gut on who comes up repeatedly, and checking collaboration tools for who gets recognized.

• Recognition is often more meaningful than money and should be public, personal, written, and reinforced during reviews.

• Top performers should never have to ask for raises or promotions. If they do, you’re not being proactive enough.

• Map career paths to their actual motivations, not default paths that push everyone into management.

FAQs

• How do I identify my top performers if I don’t have a formal review process? Ask every leader for their one or two best team members and watch collaboration tools like Slack to see whose names get called out repeatedly by peers.

• How do I justify paying top performers significantly more than others in the same role? Outliers are unique by definition. If someone believes they’re performing at the same level, they can come talk to you. But your top 1-3% create significant returns that justify greater compensation.

• How often should I meet with my top performers? At a minimum, once per year for the CEO. Their direct manager and head of people should also meet with them regularly. The frequency matters less than the quality of the conversation.

I used to hate board meetings. And I’m pretty sure my team and most of my investors did too.

For a long time, board meetings felt like this necessary evil. Every quarter, I’d spend multiple days preparing a deck, only to sit in a room reading slides to a board that seemed half-engaged. My team felt like they were on trial, and we’d all leave exhausted, having burned three or four hours without making any real decisions.

Board meetings felt like a governance checkbox; an obligation that pulled me away from actually running the business. And when one meeting finally ended, I’d already be stressed about preparing for the next one in three months.

I eventually realized the problem wasn’t board meetings themselves. The problem was that I didn’t know how to run them.

I’ve been a part of over 100 board meetings over the last 20 years. From running my own board meetings, attending others, and helping founders plan theirs, I’ve seen how different investors, leaders, and company stages approach them. And I’ve found a format that works.

Let me be clear: board meetings are always a lot of work. They will still be exhausting. And you’ll likely find yourself getting grilled on tough questions. But this format transforms them from dreaded obligations into productive, strategic sessions. It makes the prep work more efficient. It gets your investors engaged. And it helps you make better decisions with their input.

This article covers the exact format I use, and the logistics that will save you time and stress, enabling you to turn your board meetings into something actually useful.

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Table of contents

1. What board meetings are actually for

2. When to start having board meetings

3. The board meeting format that works

4. Preparation tips for success

5. Make your next board meeting count

What board meetings are actually for

Most CEOs treat board meetings like a status update. You present what happened last quarter, justify your decisions, and hope you don’t get grilled too hard on the metrics that you missed. But that’s the wrong way to approach board meetings.

A board meeting has five clear purposes:

1. Take care of governance items: Things like stock option grants, approval for massive vendor contracts, compensation changes for executives, approval of your annual operating plan, etc. These are the legal and fiduciary decisions that need board approval. Get them done efficiently so you can move on.

2. Alignment around the current state of the business: The financial results from last quarter, what went well, what didn’t, and what you’re focused on this quarter. This should be equal parts qualitative and quantitative.

3. Discuss strategic initiatives and decisions: Are you changing your ICP? Considering a product pivot? Planning for your next round of funding? Did your competitor make a big announcement recently that changes the playing field? Are you thinking about adding key executive roles? These are the topics that benefit from board input.

4. Make explicit asks of board members: Tell them exactly what you need. Maybe it’s an introduction to a prospective customer, candidates for your VP of Sales role, or connections to other investors for your Series B.

5. Get feedback from the board: Ask the board how they feel about your performance, your team’s performance, and the strategic direction you’re heading. This should happen in a structured way, not as random interruptions throughout the meeting.

When you structure your meeting around these five objectives, everything about the meeting changes: your board members come prepared, your team presents strategically rather than defensively, and you actually leave the meeting with clarity on the decisions that matter.

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When to start having board meetings

If you’re at a seed stage or earlier, you probably won’t have a formal board yet. That’s normal. But I’d still encourage you to adopt some version of this format for your investor updates and quarterly reviews. Why? Because it forces you to think strategically about your business, create a rhythm of accountability, and prepare you for when you do have a formal board.

The goal is to engage your investors strategically without requiring a ton of extra work. Start with a 1-hour session. As you grow and add board members and executives, those meetings will naturally expand to two, three, even four hours. But the format scales with you.

The board meeting format that works (~4 hrs)

Here’s the format I use. It’s structured so you move from administrative necessities to strategic conversations, and it ensures your board actually helps you rather than just observes.

1. Corporate matters

Duration: 10-15 minutes | Who: CEO, board members

Start with just your board in the room or on the video call if it’s remote. This is where you handle sensitive governance items, such as stock option grants that require approval and any major commitments that require board sign-off. For example, a massive contract with AWS or Azure that crosses your approval threshold, or an executive comp package that goes beyond your normal range.

You can handle some of these via email, but you should check with your lawyer on what approvals need to happen in vs. out of the board meeting. Most law firms that work with venture-backed companies will send their lawyer to your board meeting for free just to listen and take minutes. If that’s an option, do it.

2. Mission reminder

Duration: ~2 minutes | Who: CEO, executives, board members

Now, bring in your executive team or functional leaders (C-level execs or VPs running major functions like sales, marketing, success, product, engineering, etc). Not everyone does this, but I believe it’s important for a few reasons:

First, it builds accountability. Your leaders aren’t just reporting to you anymore. They’re presenting their results directly to the board, which changes how they think about their work. Second, it’s a huge career growth moment for leaders who have never had to speak in front of a board. And third, it gives board members exposure to your leadership team and drives alignment amongst your own team.

Before diving into the business, I like to remind everyone why we exist. Your board members are likely invested in several other companies. They’re busy, so it’s always good to refresh their memory on what your north star is. Show the mission statement and remind them of the grand vision.

This might sound cheesy or repetitive, but it works. Board meetings get tactical fast. Spending a couple of minutes reconnecting everyone to the mission sets the right tone for the strategic conversations ahead. It reminds your board why they invested in the first place.

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3. State of the business

Duration: 20-30 minutes | Who: CEO, executives, board members

This is your section as CEO to explain to the board where the business is today. Cover what went well last quarter, what didn’t, and what you’re focused on this quarter. Share what’s on your mind and how you’re thinking about the business.

I like to include the strategic objectives we set at the beginning of the year. Then have your head of finance or CFO present the financial results as well as an outlook for the rest of the year. Talk about ranges you could end up in and what will drive overperformance or underperformance.

It’s important that in this section and throughout the entire board meeting you’re being transparent about the good, bad and ugly. Every company has issues, your board members know that, it’s better to be upfront about those things.

4. Departmental updates

Duration: 45-60 minutes | Who: CEO, executives, board members

This is where each functional leader presents their area using the same format. I use a four-box approach.

• Top left: What went well

• Bottom left: What didn’t go well

• Top right: Top five KPIs for that department (mark them green, yellow, or red)

• Bottom right: Focus for the current quarter

Then, add a slide or two of trending KPIs for each functional area. Keep these consistent quarter to quarter so that everyone gets used to talking about the same metrics.

Finally, include one or two detailed slides with additional color for each functional area. Maybe you attended a conference and got some really good feedback, or your product team shipped a huge feature customers have been asking for. Show them some photos, stats, or a live demo. Or it may be additional color commentary on one of the KPIs that needs more explanation.

5. Strategic topics

Duration: 60-90 minutes | Who: CEO, board members, execs optional

This is where you spend the most time and get the most value. Pick two or three big topics that need deep discussion. These could be:

• Fundraising updates: where you are in the process, feedback you need on valuation and targets

• Org structure: what roles you need to hire, changes to how your team is structured, and asking for connections

• Product strategy: a pivot you’re considering, changing your ICP, or major roadmap decisions

• M&A: companies you’re looking at buying and the strategy behind acquisitions

• Go-to-market shifts: changing your sales model, expanding into new segments

Spend 20 to 30 minutes on each topic. For big decisions, you might spend an hour. Depending on the subject, keep your execs in the room or ask them to step out. Use your judgment.

This is the part of the meeting where your board members can have a big impact. Remember, they’ve seen other companies go through what you’re going through. Lean on them, ask for feedback, and let them bring ideas to the table.

6. Asks from the board

Duration: 5-10 minutes | Who: CEO, board, execs optional

Make your asks explicit. Don’t hint, and don’t assume they’ll offer.

Tell them exactly what you need: “I need an intro to the CRO at Salesforce.” “I’m looking for candidates for our VP of engineering role, specifically someone who’s scaled a team from 10 to 50.” “I want to talk to three other founders who’ve gone through a Series B in the last six months.”

Include these in the deck so they’re top of mind. Take notes on which board members raise their hand for which ask, then follow up with them individually after the meeting. You’ll be surprised at the results of simply asking for what you need.

Pro tip: At your next board meeting, give a shoutout to the board members who followed through. Recognition reinforces the behavior, and it sets expectations for everyone else.

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7. CEO and board session

Duration: 15-20 minutes | Who: CEO, board members

If you have not done so already, now ask the rest of your team to leave the room. This is where you get feedback on the board meeting and other parts of the business. Ask board members, “How do you think the meeting went?” “How do you feel about the executive team’s performance?”

Be direct. You might get some tough feedback from them, but that’s what you want. As CEO, you’re in the weeds day to day; the value of a good board is bringing outside perspectives and helping you course-correct when needed.

8. Board-only session

Duration: 5-10 minutes | Who: Board members only

At this point, you exit the room. You need to give the board time to talk without you present. But one board member should be designated to call you afterward and provide feedback.

For example, one time I got feedback from a board member that I’ll never forget. They said, “Dave, we love your excitement. We know you have all sorts of ideas about where you could take the product, but you’re all over the place right now. You need to get more focused and drive execution. ” They were right.

Or the board may have concerns about a particular team member. Whatever the case, give them time to talk and make sure they close the feedback loop with you so you stay aligned.

Board members value this short session because it allows them to calibrate and see how each other is feeling. It gives them a chance to gauge whether they’re overreacting to something or if everyone is thinking the same thing.

Some boards prefer to do this in the CEO and board session but I feel that doing it this way ensures you’re getting the most raw and real feedback.

Preparation tips for success

How you prepare for a board meeting can make the difference between a productive session and a waste of everyone’s time. Follow these tips for success:

Schedule all meetings at once

Set up all your board meetings for the year at the end of the previous year. Get them on everyone’s calendar in one shot. It’s hard enough finding dates that work for multiple investors. Trying to schedule each meeting during the quarter it happens is a nightmare and will result in constant scheduling conflicts.

The length of the meeting depends on the size of your company. For early-stage companies, you can accomplish everything in 90 minutes. As you begin to grow, you’ll probably need 2 or 3 hours. For later-stage companies, you might need 4 hours or more. It really depends on the number of board members and how mature your company is.

Pro tip: Schedule board meetings at least three weeks after the quarter ends. You need time to close the books, prepare the deck, and align with your team on the current quarter’s priorities.

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Send the deck ahead of time

Send the deck at least 48 hours before the meeting and tell your board members that you expect them to review it before the meeting starts.

Ask them to flag topics or questions in advance of the meeting. They’ll rarely do it, but it’s helpful to know if there is a big topic you and your team should prepare for. Pushing people to read the deck ahead of time eliminates surprises, and allows you to spend less time on the state of the business, and more time on the strategic, higher leverage conversations.

Don’t change the deck once you send it. If you need to clarify something or add color, make a note of it and address it in the meeting.

Finally, don’t spend three days making a beautiful deck with animations. Your investors don’t want that. They want substance and clarity. An ugly deck that’s impactful is better than a beautiful presentation that lacks depth.

Pro tip: Store all decks in an organized folder. You’ll reference them more than you think.

Get your leaders ready to present

Once you know which leaders will be presenting, make sure they’re prepared. Give them a rundown of how the meeting will flow, and brief them on who the board members are so they understand their audience. Then, make sure they understand the ground rules:

• If they don’t know the answer to a question, they shouldn’t guess. They should say, “I’ll get back to you on that,” and follow up after the meeting.

• This isn’t a leadership team meeting. They shouldn’t challenge other leaders in the room.

• The main goal is to share what they’re working on, what they’re thinking about, and get feedback from the board.

Your leadership team might be great operators, but presenting to a board is different from day-to-day work. Make sure your team is prepared, and that you answer their questions ahead of time.

Pro tip: Do a dry run with your leadership team before the meeting and before you send the deck (in case you want to make any changes). Discuss the tough questions that might come up. These prep sessions often identify some level of misalignment that should be addressed before the board meeting.

Make your next board meeting count

Board meetings don’t have to be something you dread. They also don’t have to be performative exercises where you defend last quarter’s numbers while your investors check their phones.

When you structure them right, board meetings become one of the most valuable tools you have as a CEO. You get strategic input on the decisions that actually matter. You make explicit asks and get real help. Your team sees you operate at the highest level of the company. And you leave with clarity instead of anxiety.

The format above works because it’s built around what board meetings are actually for: governance, alignment, strategic discussions & asks, and feedback. Follow this structure, do the prep work, and you’ll transform these quarterly obligations into sessions you actually look forward to.

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Key takeaways:

• Board meetings have five clear purposes: handle governance items, align on the current business state, discuss strategic initiatives, make explicit requests, and get feedback from your board.

• Schedule all board meetings for the year at once, at least three weeks after each quarter ends, to allow for closing books and deck preparation.

• Use a consistent format across board meetings, and send your deck to all attendees 48 hours before the meeting.

• Spend the majority of your meeting time on two or three strategic topics that require in-depth discussion and board input.

I didn’t know what a leadership 360 was when my head of people, Emily Connery, first suggested we do one.

“We’re going to collect feedback from all the people who report to you,” she explained. “The people who interact with you regularly, and key people across the organization. We’ll gather it in an anonymous way where they can really speak their thoughts about where you’re strong, where you’re weak, and where you can improve. Then we’ll consolidate it and present it back to you.”

At first, I didn’t get it. I thought I was pretty self-aware and that I knew where I was good and where I needed improvement. I thought people liked working with me for the most part. Of course, I didn’t appreciate why she was suggesting this: she had feedback for me and she knew other people did too.

But it’s very hard for someone to sit across from you and tell you the hard stuff when you’re the CEO. Even though you might think, “I’m just like anyone else here,” to someone else, they’re thinking, “This is my boss. This person could fire me. They could choose not to promote me. They could hold a grudge against me because I said this.”

The reality is that I can count on one hand the number of people who have given me honest, candid feedback face-to-face.

The leadership 360 is a way of surfacing what you need to hear from everyone else.

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Table of contents

1. What is a leadership 360?

2. Why CEOs need 360 reviews more than anyone

3. How to conduct a 360 leadership assessment

4. The hard part: receiving the results

5. What I learned and how I adjusted

6. Share the results

7. Tips for success

8. Do this at least once

What is a leadership 360?

A leadership 360 is the process of collecting anonymous feedback from the people who work most closely with you. It’s both qualitative and quantitative, meaning you get numerical ratings and written explanations.

The head of people or a third-party team meets with each person you work closely with and asks them to rate you on a scale across a broad range of leadership behaviors and effectiveness areas. Usually, it’s a 1-4 or 1-5 scale.

For each rating, there’s a follow-up: “Why not a four?” or “Can you explain that?” This qualitative part is where the real insights come from.

At BetterCloud, we started with doing a 360 for me as CEO. Once we saw how valuable it was, we expanded it to every C-level executive. Eventually, we did it for every VP-level person and anyone with a sizable team.

But the CEO 360 is critical because you’re the person who receives the least candid feedback on a day-to-day basis.

Why CEOs need 360 reviews more than anyone

Most CEOs don’t realize their feedback is almost always filtered.

The irony is that the more visible you are, the more people you impact, and the harder it becomes for anyone to tell you the truth. Leaders affect the most people but get the least honest feedback.

You might have an open-door policy. You might pride yourself on being approachable. You might believe people tell you what they think. But the reality is that people are terrified to give you honest feedback. A 360 review bridges that gap.

Demonstrating vulnerability is one of the most powerful things a CEO can do

Many CEOs say they are open to a 360 leadership assessment, but six months later, nothing has been done. It’s not because they forgot. It’s because it’s genuinely scary. You’re opening yourself up to hearing some really tough feedback when you do this.

I’ve seen an executive get their 360 results back and score 1.5 out of 4 on almost everything. The synthesized feedback from their team basically said: “We don’t trust you.” That’s brutal. There’s no more plausible deniability. There’s no more “no one ever told me that.” You have to sit with it.

Vulnerability promotes a growth mindset. When you exhibit vulnerability as CEO, it signals that it’s okay to admit mistakes. It creates an appetite for risk-taking because people see that failure and improvement are part of the process. It encourages sharing feedback because you’ve modeled what that looks like.

The truth is, if you want your team to keep pushing themselves to get better, you have to keep pushing yourself to get better. And if you want your leaders to undergo a 360 review, you have to do it first.

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You must grow alongside your company’s growth

Your company will be a completely different organization every year or two, depending on your growth rate. I’ve seen the inner workings of some of the fastest-growing AI companies, and they feel like new companies every quarter or two due to sheer growth. The best CEOs and leaders are the ones who can keep pace and grow at least that fast themselves. Otherwise, at some point, your company outgrows you, and it all breaks down.

A leadership 360 forces you to confront how you’re actually perceived. And for most people, that’s terrifying.

How to conduct a 360 leadership assessment

The process is straightforward, but it requires a trusted person to execute it well. Here’s how to do a leadership 360 assessment.

Step 1: Delegate someone to run it

Your head of people or HR director often coordinates and runs this. They need to be someone you trust, someone who can extract nuance from conversations, and someone who can deliver tough feedback well.

Running a leadership 360 well requires a lot of time, energy and bandwidth. There is also lots of nuance in properly conducting team interviews, and so it often helps to have a third party run them for you and your executive team. This is something that we have started to do at Not Another CEO for clients; if you are interested you can reach out to my partner Nick (email nick@notanotherceo.com or click below).

Tip: The key is to choose someone who you and your team trust. If people don’t trust the person running it, they won’t be honest.

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Step 2: Identify who to interview

Don’t just follow the org chart. You need feedback from the people who actually know how you operate, no matter where they sit in the organization.

Your head of people should interview all your C-level or direct reports, obviously. But they shouldn’t stop there. They should also include other key people you regularly interact with. Maybe there’s a VP you work closely with, or someone who’s been at the company since the beginning, or people who’ve seen you in action across different situations. Maybe it’s an IC who worked on a special project with you.

Tip: Don’t be too broad in your interview selection. Focus on the people who genuinely understand how you work, so you get the richest results. Some people include investors in this process. Personally, I’d skip that, especially for the first 360. Keep it focused on the people you work with day-to-day.

Step 3: Conduct the interviews

The interviews should be done one-on-one, either in person or via Zoom. This isn’t something you can do over email or with a survey tool. You need the nuance that comes from a real conversation.

Your interviewer should review each category they’re measuring and ask 3-5 questions per category.

The categories and competencies

A typical 360 covers competencies across multiple categories, such as team leadership, vision and strategy, culture and collaboration, adaptability, execution, decision-making, business judgment, self-awareness, and coachability. You might target other categories outside of that, but those are a great starting point.

Here’s what people evaluate across those categories. The person being interviewed ranks each one on a scale of 1-4, and answers follow-up questions for each to get rich qualitative insights.

Team leadership:

• “Builds an effective executive team.”

• “Creates an environment that fosters healthy debate and collaboration.”

• “Consistently supports and encourages your team to achieve their goals.”

Decision-making:

• “Makes sound decisions even with incomplete information.”

• “Makes decisions that demonstrate sound business judgement and rationale.”

• “Is objective in making decisions.”

Culture and collaboration:

• “Provides insightful and timely feedback to help talent development.”

• “Is effective in their pursuit to work collaboratively with key stakeholders to drive the strategic goals of the business.”

• “Is a role model in upholding our company values.”

Self-awareness:

• “Demonstrates awareness of their impact on others.”

• “Continues to be ready and willing to learn; desire outstrips ego.”

• “Regularly plays to strengths and can admit mistakes.”

Vision and strategy:

• “Creates and articulates a compelling vision for all stakeholders.”

• “Sets clear priorities for the company and his/her executive team.”

• “Communicates clearly with priority changes.”

Execution:

• “Follows through and holds the team accountable for delivery of committed priorities.”

• “Drives the strategic goals of the business with intention and focus.”

• “Has the expertise necessary to manage this function.”

Rating and follow-up questions

For each category, they ask for a rating using a scale. For example:

1 = Limited demonstration: you’re not good at this

2 = Actively working to improve: you’re trying, but not there yet

3 = Standard: what you’d expect at your level

4 = Consistent world-class: you’re exceptional at this

Then they ask follow-up questions to get the qualitative side: “Why not a four?” or “Can you explain that rating?” or “Is there a specific example you can think of when they displayed this behavior?”

That follow-up is where the real information comes out. Someone might rate you a three on driving accountability. But when they’re asked why it’s not a four, they explain that you’re great at holding people accountable one-on-one, but you don’t do it in group settings. That’s the insight you need.

Tip: Do a self-assessment as part of this. I did this in one of my 360s, and it was interesting to see where my perception of myself lined up with everyone else’s ratings (and where it didn’t).

Step 4: Synthesize and package the results

Once all the interviews are complete, your head of people needs to compile all the findings. They’ll need to aggregate quantitative scores across all respondents and synthesize qualitative feedback into themes.

Everything needs to stay completely anonymous. The point is to provide a safe opportunity for your peers to share feedback and for you to use those insights to improve.

The final report should show you your scores across each category, along with the qualitative themes. The key is to boil all of this down into something actionable: “Here are the three things you do really well. Here are the three things the team thinks you could improve. And here’s how they’d like to see you improve.”

Tip: The final report doesn’t need to include every single piece of feedback. That could be too overwhelming and dilute the most critical insights. Focus on the patterns and themes that matter most.

Here’s the summary page from one of the leadership 360 that was conducted for me:

The hard part: receiving the results

You should receive results in a one-on-one setting. It’s hard to receive this kind of feedback. You need someone who can deliver it well. Again, this is why you need someone you trust to run this.

They need to present the data, explain the themes, and address the feedback without identifying who said what. You should do your best not to ask who said what, even though you’ll be trying to guess in your mind. Respect the process and keep it a safe and anonymous way to get feedback.

They also need to be able to pull out the nuance. For example, if someone rated you a three, they need to know if that’s a solid three or whether they were being generous and it’s actually closer to a two.

When 10 or 15 people all say the same thing about you in anonymous one-on-one settings, that’s how they view you, and that’s most likely how the broader company sees you. That’s reality. It doesn’t matter how you view yourself.

You’re confronted with the reality of how your team actually perceives you. But when this is done well, you’ll walk away with clarity you’ve never had before.

What I learned (and how I adjusted)

When I got my 360 results back, there were some things that hit me hard. I want to share a few of them because it helps to see what this actually looks like in practice.

I wasn’t driving healthy conflict in group settings

I could challenge people one-on-one. But in group settings, I wouldn’t call someone out if they didn’t deliver.

The result? When my team saw someone not pulling their weight, they wondered whether I was holding them accountable. I was in my one-on-ones, but not those meetings. From their perspective, it looked like I was letting things slide.

Once I received that feedback, we created new systems in our leadership team meetings to drive healthy conflict. And I got better at it.

I was having conversations with ICs that caused chaos

I’d be at the lunch table brainstorming with someone who reported to one of my directs. “What if we did this? You think we could?” They’d say yes, then go back to their desk and start working on it. Their manager had no idea what was happening.

I didn’t understand the power of my words as a CEO. I was just thinking out loud, but people took it as a directive.

After that feedback, I started caveating every conversation with “I’m not telling you to do this. I’m literally just brainstorming.” It changed how I interacted with ICs and helped me avoid accidentally disrupting momentum.

I would jump in and take the reins when I got stressed

Whenever things got stressful, I’d try to take over from people who were already working on solutions. But when you jump in like that, you derail the processes and systems they’ve built. You’re not helping, you’re creating chaos.

I had to become aware of this and catch myself when I felt that urge.

Share the results

Here’s the crucial step that most CEOs skip: you need to share the results. Don’t just get the feedback, process it privately, and move on. That misses the entire point.

Share it with your leadership team and conduct 360s on them

At your next leadership team meeting, show up and say something like this: “I want to thank everyone for giving feedback. Some of it was hard for me to hear, but I really took it to heart. I heard from all of you that I need to work on X, Y, and Z. I’ve processed that feedback and agree with it. I’ll start working on this. Please hold me accountable.”

This is incredibly hard to do. You’re acknowledging to your team that you’re not Superman or Superwoman. You’re admitting you have weaknesses. You’re committing to change deeply embedded parts of your personality. And the reality is, you won’t fix all of them completely. But when people see you become aware of how these things impact them and watch you try to improve, they appreciate the effort.

When you do this, you show vulnerability to your team. You show them you want to get better. And you lead by example.

Now you can turn to your leadership team and say, “We’re going to do these same 360 reviews for all of you. And I want you to do the same thing I just did: share it with your team.”

This is what defines a growth mindset, and it will change your culture.

Then share it with your entire company

If you want to go the extra mile, share the results with your entire company at an all-hands meeting. I did this at BetterCloud. I told the whole company about the feedback I received and what I was going to work on. It was very challenging, but it was worth it.

Even if you don’t improve perfectly, doing the exercise matters. It gives people the opportunity to provide feedback that you wouldn’t get otherwise. It shows them you value their input.

Tips for success

Here’s what you need for this to work:

• A trusted person to run it: either your head of people or an external firm

• True anonymity: people need to feel safe being honest

• One-on-one interviews, not surveys: you need the nuance

• A good set of criteria: these should span across key leadership categories

• Strong synthesis: you need to turn all of that feedback into actionable insights

• Courage: to hear the feedback, and to share it with your team

Do this at least once

If you’re a CEO and you’ve never done a 360 review, you need to do this at least once. It will help you in your current company, in future companies, and in your life. You’ll understand how you’re perceived in a way you never have before.

After you’ve made improvements, repeat the process in a couple of years. Each time gets harder because you’ve already tackled the low-hanging fruit, and now you’re working on the core DNA issues, the deep stuff, the hard stuff. But that’s the progression: do it, improve, do it again, improve. It’s exhausting, but it’s incredibly impactful.

Key takeaways

• CEOs rarely get candid feedback. 360 reviews surface what you need to hear.

• A leadership 360 assessment uses anonymous interviews with direct reports and key stakeholders, rating you 1-4 across leadership categories with qualitative follow-ups.

• Your head of people or another trusted party conducts one-on-one interviews, synthesizes feedback, and delivers results highlighting three strengths and three areas to improve.

• Receiving the results is hard: when 10-15 people say the same thing about you anonymously, that’s how they actually view you.

• Most CEOs skip sharing the results, but that’s how you build trust and get accountability.

• Do this at least once as a CEO: it will help you in your current company, future companies, and your life.

FAQs

How long does a 360 review take to complete? Plan for 3-6 weeks total. The interviewer needs time to schedule and conduct 10-15 one-on-one interviews, and each takes 30-60 minutes. Then they need to analyze the feedback, package the results, and deliver them.

Should I use an external firm or do it internally? If you have a strong head of people you trust, doing it internally is often the best option. They know your organization and can ask better follow-up questions. But doing it internally also requires a lot of energy, time and bandwidth; when you cannot dedicate a trusted internal resource to do this, find a trusted third party.

How do I ensure the feedback stays truly anonymous? The interviewer should never reveal who said what. They need to synthesize feedback into themes and aggregate quantitative scores. They should interview at least 10 people so individual responses can’t be traced.

I’ve spent the last couple of years meeting with hundreds of CEOs and founders, and when I sit down with them one-on-one, many open up about struggling with imposter syndrome.

First-time founders chasing product-market fit feel it. And serial CEOs running companies doing hundreds of millions in revenue feel it. Success, age, or experience doesn’t matter.

At BetterCloud, after we’d raised over $180 million, had over 350 employees, an A-list executive team, over 2,000 customers, and rapid revenue growth month over month, I remember thinking: “Am I equipped to run this kind of company? Do I deserve this much trust from world-class investors? Why would these experienced executives want to work for me? Am I delivering what our customers actually need?”

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There were days when I felt pretty confident about these things, but then there were days when I questioned it all.

What I’ve learned from those hundreds of conversations and my own experience is that imposter syndrome doesn’t go away. And the chances you will experience it as a company leader are nearly 100%. It’s how you choose to deal with it that makes all the difference.

Imposter syndrome will either crush you or drive you. It will slow down your decision-making and paralyze you, or it will push you to get better, to overachieve, and to prove you deserve the position you’re in.

This article explores how to react to those uncomfortable feelings that imposter syndrome brings and treat them as fuel for growth and success.

Table of contents

1. What is imposter syndrome?

2. Every CEO battles imposter syndrome

3. There are two paths: paralysis or fuel

4. How to channel imposter syndrome into growth

5. What other CEOs say

What is imposter syndrome?

Here is the definition from Webster’s dictionary:

Imposter syndrome is a psychological condition that is characterized by persistent doubt concerning one’s abilities or accomplishments accompanied by the fear of being exposed as a fraud despite evidence of one’s ongoing success.

Every CEO battles imposter syndrome

Anyone with a shred of self-awareness will experience imposter syndrome as a CEO. Of course, it’s a spectrum, but I genuinely believe most people (especially high achievers and company leaders) experience it to some degree.

The common lie people tell themselves is that they’ll eventually “get past it”. They think once they hit a certain revenue milestone or notch a few wins, the self-doubt will disappear.

It doesn’t. If anything, imposter syndrome intensifies as the stakes increase.

As Michael Cannon-Brooks, co-founder and CEO of Atlassian, said in a TED Talk about imposter syndrome: “Most days, I still feel like I often don’t know what I’m doing.” Here’s someone running a multi-billion dollar, one of the most successful software companies of all time, and he’s openly talking about feeling like a fraud.

It doesn’t matter who you are or what you’ve accomplished. These feelings don’t go away. You’re constantly stepping into roles and making decisions you’ve never made before.

Watch the full TED Talk from Atlassian’s CEO and co-founder here:

There are two paths: paralysis or fuel

When imposter syndrome hits, you’re standing at a fork in the road. You can take one of two paths.

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Path one: paralysis

This is where imposter syndrome becomes your enemy. It slows you down and makes you second-guess everything.

I’ve seen this play out with many CEOs. They start questioning their gut instincts because they assume someone else must know better. The investor must know better because they have access to billions in capital. The CRO must know better because they have 20 more years of experience. The customer must know better because they’re an executive at a larger company.

When you let imposter syndrome win, you end up in a place where you’ve lost trust in your own intuition. You think there’s no chance your gut can be right. You feel like you’re getting away with something and that someone’s going to “find out” you’re a fraud.

The result? You slow down decision-making because you’re thinking about what others think. You avoid risks out of fear of potential consequences. The worst part is that this insecurity creates a ripple effect, making the entire organization feel less confident and effective.

So you freeze.

Path two: fuel

This is where imposter syndrome becomes your competitive advantage. Instead of letting it paralyze you, you channel it into fuel.

I recently sat with a Buddhist monk in Thailand who said something that stuck with me: “Thoughts themselves are neutral. They’re not inherently good or bad. It’s only when we assign them meaning that they take on that value.” In other words, imposter syndrome is just a thought. The question is, what value are you going to give it?

The CEOs I’ve seen take this path treat imposter syndrome as a chip on their shoulder. It pushes them to constantly get better, to prove, without a shadow of a doubt, that they deserve their position.

But there’s a wrong way to do this, and it’s overcompensating. I’ve worked with CEOs who use imposter syndrome as fuel, but they take it too far. Everything becomes about proving they know something, and it comes across as ego rather than confidence. They’re so self-conscious about appearing inadequate that they swing hard in the opposite direction.

When channeled properly, imposter syndrome actually brings you back down to earth. It lowers your ego and makes you a better listener and more grounded leader.

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How to channel imposter syndrome into growth

If you’re going to have imposter syndrome anyway (and again, you will), you might as well make it work for you. Here’s what that looks like in practice.

Recognize it as a signal you’re growing

Imposter syndrome shows up when you’re stepping into something new, something that feels uncomfortable because you haven’t done it before. That discomfort isn’t evidence that you’re failing. It’s evidence that you’re pushing beyond what you already know how to do. And it’s also evidence that you care, that it matters to you that you’re successful and that you don’t want to disappoint others.

The difference between paralysis and fuel comes down to how you interpret that discomfort. Do you see it as proof you don’t belong? Or as a sign you’re precisely where you need to be (in the uncomfortable zone where real growth happens)?

This mindset matters. If you can’t channel a growth mindset, imposter syndrome will take a serious toll on you (and your team).

Identify the specific skill gap it’s pointing to

When imposter syndrome hits, ask yourself: “What specifically am I feeling unprepared for? What skill or knowledge gap is this exposing?”

I recently spoke with a CEO I’m mentoring who’s dealing with this. His mindset: “I have to get better. I have to keep up with the growth of this company.” He’s using imposter syndrome to identify exactly where he needs to develop, then actively working to close that gap.

One thing imposter syndrome highlighted for me was public speaking. I always felt like the audience knew more than me or would challenge the points I was making. That feeling forced me to get much better at public speaking and to feel confident that I was indeed an expert.

Another example: As BetterCloud grew, I started to feel disconnected from our customer base. When I’d talk about what we should build or what customers needed, I felt like my team was questioning me. (I found out later they weren’t, it was the imposter syndrome talking.) But that drove me to literally meet with 100 customers in 100 days. I came away with a ton of insights, stronger customer connections, and most importantly, the confidence that my intuition was right.

Use it to stay humble and keep learning

The best CEOs I work with are constantly asking for feedback. “What am I doing well? What am I not doing well?” They’re never satisfied with their own growth. They always feel like they’re behind.

That feeling can actually make you better to work with because it lowers your ego. It makes you listen more carefully. It keeps you open to learning from your team, your board, and your customers.

This is where having a strong CEO support system becomes critical. You need people who can give you honest feedback, challenge your assumptions, and remind you that you’re not alone in these feelings.

Let it create healthy paranoia

There have been moments when I thought, “What if the board fires me?” I know other CEOs have thought this as well.

That paranoia isn’t necessarily healthy on its own. But it drives me to overachieve, to prove I deserve the opportunity, to make sure I’m doing everything I can to earn my seat at the table.

Flint Lane, the CEO and founder of BillTrust, told me he was bullied in middle school. That created a serious drive in him. He built his company partly to prove he was worthy of success, and he sold it for almost $2 billion. And then he started another company. That need to prove himself gave him unlimited stamina. He’ll always be pushing to get better and to achieve more.

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Imposter syndrome isn’t going away

You’re going to feel imposter syndrome tomorrow, next month, when you raise your next round, when you hit your next milestone. The feeling doesn’t care about your track record or how many times you’ve proven yourself.

Here’s what you can control: how you react to the feeling. You can let it freeze you up, slow down your decisions, and make your team question whether they should follow you. Or you can use it as fuel and let it drive you to get better, to stay humble, and to prove you deserve what you have. The path you choose makes all the difference.

Key takeaways

• Most, if not all, CEOs experience imposter syndrome.

• Success, age, and experience don’t make it go away. If anything, it intensifies as the stakes increase.

• Imposter syndrome will either paralyze you or propel you. The difference comes down to how you choose to respond.

• Your team feels your confidence (or lack of it), so if you let imposter syndrome paralyze you, it will trigger the same feelings in them.

• Use imposter syndrome to identify specific skill gaps, drive continuous learning, and stay humble enough to listen.

FAQs

Is imposter syndrome the same as self-doubt? They’re related, but imposter syndrome is more specific. It’s not just doubting a single decision; it’s a persistent feeling that you don’t deserve your position and someone’s going to figure that out eventually.

When does imposter syndrome become a problem? When it paralyzes you. If it’s slowing down your decision-making, causing you to second-guess every call, or preventing your team from feeling confident in your leadership, it’s working against you.

Does imposter syndrome ever go away? No. And Michael Cannon-Brookes is a great example. He runs a multi-billion-dollar company and still feels it. The goal is to channel it into growth instead of letting it slow you down.

The worst part about being a leader is having to fire someone.

It never gets easier. It always sucks. I’ve never walked away from letting someone go and thought “that was fine.”

The first time I had to fire someone, I couldn’t sleep for two nights leading up to it. I had delayed it for months because I was terrified. I liked the person, and I was worried about what would happen to their career. These feelings are natural for any human with empathy.

When I finally fired them, they were shocked. They genuinely thought they were doing a good job. It wasn’t fair that they were caught offguard, and it was 100% my fault.

The reality is, if you want to build a high-performing team, you must learn how to fire someone the right way. Even if you’re a really good interviewer, you’re only going to get it right some of the time. As Ryan Simonetti, President and CEO of Convene Hospitality Group, shared, “I still think hiring is the hardest thing. And even if you’re world-class, you’re probably only batting like .400.”

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Phil Hernandez, CEO of Marketo, also shared the complexities of hiring and how getting it right 100% of the time is impossible:

This article covers the process I use to manage performance and remove the element of surprise. Following it won’t make firing easy or painless, but it will ensure the employee isn’t blindsided and boost your confidence as you navigate these difficult (and inevitable) conversations as a leader.

Table of contents

• The spectrum of firing

• Why people delay firing

• Step 1: Set expectations at the offer

• Step 2: The first 90 days

• Step 3: When performance slips

• Step 4: The second warning

• Step 5: The termination meeting

• It’s about fit, not failure

• What other CEOs say

The spectrum of firing

Not all firings are the same. There’s a spectrum, and understanding where your situation falls helps you choose the right approach.

Instant terminations

On one extreme are instant terminations. I once had someone send a derogatory email to the entire company at 2 am. They meant to send it to one person, but hit the company-wide distribution list. My head of people and I waited at the elevator door the next morning and let them go on the spot. I once had a sales rep game the commission system by buying the product on their credit card, canceling the card, and collecting huge commission checks for months. These situations require immediate action.

Mutual exits

On the other extreme are mutual exits. These typically involve long-tenured employees who have been with your company for years, but the company has outgrown them, or they’ve outgrown their own role. These people have given everything to your company. They deserve a different conversation, where you work together on a transition plan, potentially with higher severance and time to find their next opportunity.

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Melanie Fellay, CEO of Spekit, on how some employees don’t grow at the same pace as the company:

Performance issues

Most cases fall in the middle of those extremes. In these situations, the person isn’t performing, and it’s not mutual, but it’s also not instantaneous. This is what the rest of this article focuses on. These are the people you know have potential but are not properly contributing and require some course correction.

Why people delay firing (and why you shouldn’t)

I’ve coached dozens of first-time managers and CEOs on how to fire someone, and almost all of them delay it just like I did early in my career. After seeing this time and time again, I’ve noticed some patterns in what holds them back. It always stems from these fears:

The first fear is purely of the conversation itself. You’ll lose sleep. You’ll feel sick. This fear is natural, and honestly, it never fully goes away. But you can’t let it paralyze you.

The second is fear of backfilling. “This person isn’t the best, but they’re keeping the seat warm. If I fire them, who’s going to do the work?” The reality is that a mediocre person in the seat is worse than an empty seat. They’re preventing you from finding someone great, and they’re dragging down everyone around them.

The third is personal. Maybe you hired a friend, or you’ve worked with this person for years and genuinely like them. You’re wondering: will they hate me? Will this end our friendship? This is real, but your job as a manager is to do what’s best for the team, even when it’s hard.

The fourth is worrying about the team’s reaction. I’ve worked with CEOs who are terrified that every single firing will make the entire company think layoffs are happening or that firing a team leader will undercut morale. But your team is smarter than that, and they probably already know this person isn’t performing.

The fifth is questioning yourself. “Do I have enough reason to fire them?” If you’re asking yourself this question, you already know the answer.

All of these fears are real. But delaying only makes the situation worse for you, for the person, and for your team.

Step 1: Set expectations at the offer

The firing process doesn’t start when someone’s performance slips. It starts the moment you give them the job offer.

The hiring manager should make the offer call. Not HR or the recruiter. This is a critical moment in the manager-employee relationship. During this call, I always start by identifying 2-3 “yellow” flags that came up during the interview process.

Here’s an example: “We really enjoyed our meetings with you. However, when we circled up as a team, there were two things we were concerned about. First, you’ve never worked at a company this size, and even though you said you’re ready to get your hands dirty, you’ve always had a large team supporting you. Second, you’ve never marketed to our target audience. Marketing to CMOs is very different from marketing to SREs. That said, we think you’ll overcome those things. If you do, we’re sure you’ll crush it. So with that, we’d love to have you join the company.”

I’ve never interviewed someone where everything was perfect. There’s always something. Maybe they haven’t managed a team before, they’re switching industries, or they’ve only worked at big companies. By naming these concerns upfront, you’re setting expectations from day one. The person knows you’ll be watching these areas, and if they can’t overcome them, they won’t be successful.

I’ve had people tell me years later, “I remember the three things you brought up in that call. I was so scared I wouldn’t get the job. I hope I proved you wrong.”

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Step 2: The first 90 days

On the new hire’s first day, schedule a formal 90-day check-in. Tell them clearly: “By day 90, we expect you to be performing and contributing. If there are any issues, we want to address them early.”

Leading up to this check-in, give informal feedback in every one-on-one. Share what you’re observing, give feedback on their first projects, and ask how they’re doing. Are they surprised by anything? Do they feel like they’re getting a sense of the product, market, and customer?

The 90-day check-in should be formal. Give feedback verbally and in writing. This is your system of record, and it’s a forcing function. Everyone is working towards this date.

The new hire is asking themselves: Do I even like this job? Is this what I expected? Do I feel like I’m contributing? And the manager is asking themselves: Is this person doing the job we hired them to do? Are they showing any of the yellow flags we identified in the interview process? Are they on a good trajectory? Am I happy I hired them?

I’ve had a couple of situations where both the person and I agreed at the 90-day mark that it wasn’t a good fit, and we mutually parted ways. It doesn’t happen often, but it’s an important checkpoint.

I once had a head of people who literally wanted us to be like Facebook with unlimited perks, massive budgets, all of it. At 90 days, I said, “We’re not Facebook. We’re never going to be Facebook.” We agreed to part ways. I gave her a three-month severance even though she’d only been there a short time, and she left almost immediately.

By setting expectations at the offer and conducting a formal performance check-in at 90 days, you accomplish two critical things: you immediately correct hiring mistakes and set long-term expectations that you can leverage and revisit on an ongoing basis.

Step 3: When performance slips

Someone’s performance can start to slip at any point. It could be a few months in, a year, or 5 years. You could have someone who was crushing it for years, and one day they stop performing. If performance issues last for about a month, you need to give written feedback. This is where most managers fail. Their feedback is usually too informal, too late, or not specific enough.

Instead, write an email. Start by acknowledging what they’ve achieved recently, then reiterate that you want them to succeed. This is genuinely true. Replacing someone is painful, expensive, and time-consuming, so every manager would prefer the person in the seat to turn it around.

Then, list the specific areas where they need to improve, and for each one, include three things:

1. What needs to improve and why it’s important

2. A specific example of how they’ve underperformed

3. Exactly what I want to see instead

Here’s an example:

“When you joined, we talked about the importance of learning the product. To be successful in your role, it’s critical that you can speak to customers as a true expert. What I noticed is that you haven’t been investing the time to learn the product, and the last time I saw you do a demo, it was clear that you were just reading off a script, and the customer could tell. I want you to spend the time necessary to learn the product like the back of your hand. Then, you’ll do a mock call with me where I’ll act as the customer and ask questions, push you to go to areas of the product you currently don’t know, and essentially create an environment where you won’t be able to use a script.”

The end of the message says: “It’s critical that you improve on these things in the next couple of weeks. If you have any questions, concerns, or don’t agree with any of this, please let me know.”

Before sending it, verbally walk them through the email in a one-on-one. I read it to them so they know exactly what I’m about to send. As soon as you finish the meeting, hit send.

This is such an important tactic. There’s zero question about what was said, and the process of writing down the feedback gives you time to think about what you’re going to say, and how. And now the feedback has been clearly shared with the employee: it’s written down, been shared verbally, and they’ve had a chance to ask questions.

Some people get this feedback and turn it around completely. In my experience, it’s about 10-15% of people. But when it happens, it’s magical. I’ve seen some employees who read that feedback and immediately become the best at their function.

I’ve had others who receive it, and the next day, they’re doing the exact same thing I asked them not to. Other people opt out at this point because they feel the expectations are unfair, or don’t want to improve in those areas, and just quit.

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Step 4: The second warning

If they don’t improve within a couple of weeks, you repeat the same process. Same format, but this time the tone is much more serious, and you should loop in your HR team or head of people.

Reference the previous message and the date you sent it. Make it crystal clear: “At this point, if you don’t improve on these things, we will have to let you go.”

The timeline here is measured in days, not weeks. Usually, at this point, people won’t quit; they’ll wait to be fired and hope for severance.

Here’s what I’ve learned from doing this many times: if someone is good and wants to change, they’ll take the feedback and do it after the first warning. If they don’t, it doesn’t matter how many times you tell them. They’re not going to change the fifth time if they didn’t change after the first.

Step 5: The termination meeting

If they still haven’t improved, it’s time for a termination meeting.

Include the employee, someone from HR (or another witness if you don’t have HR), and come prepared with all of the separation paperwork. Have a standard severance based on level and tenure. This avoids negotiation and ensures consistency.

Keep the meeting short. Refer to the previous messages and warnings, and acknowledge that you wanted them to succeed, but it’s clear this isn’t a good fit. Communicate that their skills and way of working will be a better fit at another company where they can thrive.

Don’t debate it. Don’t say sorry. Don’t negotiate. They might be emotional (for good reason), but you’ve made your decision and you know what’s best for the company and for them. I’ve had people walk in, sign the paperwork, and leave without any conversation because they already knew it was coming.

It’s about fit, not failure

I’ve fired people who went on to do amazing things. They became founders, leaders at other companies, made more money, and found roles they loved.

I have countless examples of this, including a CMO who was great at vision and strategy but wasn’t the strongest at execution. This is fine at a larger company with big teams and budgets, but not for a scrappy startup.

I had a customer support rep who truly cared about helping people solve problems. He was great at talking with customers, but he wasn’t good with technical products or complex issues. He was better suited to work on a less technical product.

The list goes on.

The point is: the reason for firing someone is not always that they suck. It’s often that for this company, this stage, this product, this part of their career, it’s just not a good fit. Remember that the next time you feel the fear of firing holding you back.

When you follow this framework for firing someone, you’ve given them the blueprint to succeed. If they can’t or won’t, then you’re giving them the opportunity to find a place where they will thrive.

Building a strong team is extremely hard, and it starts with your hiring process. Check out our guide on building a hiring system that works.

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What other CEOs say

Promote from within
Ryan Simonetti, Co-Founder and CEO of Convene, states that hiring remains his biggest challenge, estimating a 40% success rate and particularly struggling with external executive hires. Despite using structured assessments in hiring, he notes it often takes 6-12 months to truly evaluate an executive’s impact due to the complexity of horizontal influence and cultural assimilation.

Hire for can-do attitude
Flint Lane, Founder and CEO of Major League Table Tennis, emphasizes that a 70–80% success rate in hiring is realistic and that no one has a perfect track record. He prioritizes candidates with a demonstrated “can-do” attitude and relevant past success in the specific function being hired for. Lane assesses this through questions about difficult projects, both successful and failed, to understand mindset and resilience.

Teams are orchestras
Phil Fernandez, Co-Founder and CEO of Marketo, views hiring as assembling a complementary team rather than filling static roles, emphasizing adaptability and synergy over rigid models. He believes hiring is inherently complex, combining skills, organizational behavior, and interpersonal dynamics, making a success rate above 60% unrealistic.

Backchannel leaders 360 degrees
Nick Mehta, CEO of Gainsight, describes his executive hiring success rate as low and emphasizes evaluating a candidate’s ability to manage up, down, across, and out. He uses in-depth backchannel referencing, including inquiries into both promoters and detractors, to assess leadership impact across stakeholders.

Scaling leaders is hard
Melanie Fellay, Co-Founder and CEO of Spekit, discusses the challenges of executive hiring, citing a 50% success rate and the difficulty of scaling early leaders as company needs evolve. She highlights the risk of hiring based on desperation, overvaluing industry experience, and underestimating the importance of self-awareness and operating style fit. Successful hires at Spekit often lacked conventional credentials but aligned well with company needs and her own hands-on leadership style.

You know what sucks as a founder or CEO? Seeing a new competitor pop up that’s blatantly copying everything you do. Your product, your messaging, your API docs. Everything. And then they undercut you on price by 50%.

I’m not talking about your typical competition. I’m talking about literal copycats. They identify the leader in a space, copy and paste blog posts, and forget to remove the original company’s name. They build and name their features the same way and copy the user experience screen for screen. They use the same obscure mock user names in API docs.

You may think this sounds ridiculous, but it’s happening more and more.

I’ve been in software for over two decades, and I’ve watched the barriers to entry collapse. What used to take months of planning, hundreds of thousands in infrastructure, and a team of engineers, can now be done in a weekend. Someone recently built a DocuSign clone in two days using Cursor.

Two days.

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Here’s another one that just popped up in my LinkedIn feed:

I read something recently from Jamin Ball that stuck with me: “I’ve come to believe the idea of a long-term moat is mostly a myth, especially in this market. Moats aren’t permanent. They’re time-bound. At best, they function as a bridge. And companies either use that bridge to reach the next defensible position, or watch their moat get breached.”

He’s right. But while no moat lasts forever, some take years to build. And in a world where anyone can clone your product and copy your messaging, the ones that take the time to build something sustainable are the ones that matter.

I will start with how we got here, and then I’ll share the six things I’ve seen work to create real distance between you and the inevitable copycats.

Table of contents

1. How we got here

2. 6 strategies to set yourself apart from the competition

3. The foundation that makes it possible

4. Today’s moat is built on a foundation of trust

5. What other CEOs say

How we got here

21 years ago, when I started my career, starting a software company required real physical infrastructure.

At Vocalocity, we had to rent space in a data center and put servers in racks at that facility. Then you had to manage those servers, upgrade the software on them, upgrade the servers themselves, and make sure there was enough storage. I remember we had wiring diagrams to make sure the racks were done correctly.

This was the reality of starting a software company until the cloud era.

Then came companies like Rackspace, the cloud before the cloud. Then AWS, Google Cloud Platform, and Microsoft Azure. Suddenly, you could stand up servers anywhere in the world instantaneously. You could scale up or down based on usage. But you still had to raise tens of millions of dollars and hire large teams of engineers to build your systems.

Today, you can go to Cursor, Replit, Lovable, and literally tell it to copy an existing product. The guy who cloned DocuSign just told the AI what he wanted, and it built it. He stood up a competitor for a fraction of the cost and in a fraction of the time.

But it’s not just the software that’s easy to copy with AI. It’s everything. Your entire website. Your messaging. Your design. Your content.

Pair all of this with VC funding being more accessible than ever, powerful global distribution channels like social media, and ready-to-go payment infrastructures like Stripe. Everything you need to create, sell, market, and fund a company is more accessible than ever before.

The result? Oversaturated markets full of copycats. The thing that used to be the hardest (building the actual product) has become the easiest. Differentiation is the real challenge.

So, what are the hard things you can do to actually stand out? What sets you apart when ten companies can build the same thing in a week?

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6 strategies to set yourself apart from the competition

These aren’t quick wins or growth hacks you can implement overnight. They’re the hard things that take time, money, energy, and real commitment. But that’s exactly why they work, because your competitors can’t just copy and paste them. The strategies below are ways you can set yourself apart and they’re all centered around one thing: building trust.

1. Community building

Real community can’t be bought or copied in two days. I’m talking about the kind of community where people want to be your customer just as much for the community as they do for the product itself.

Companies like Gainsight, Marketo, Clay, and JAMF have built this. Nick Mehta at Gainsight has become synonymous with customer success because he’s spent years, day after day, advocating for customer success leaders. He’s largely responsible for creating the role of “customer success”. They host a conference every year and ultimately created a place where everyone in the customer success space felt they needed to be. And JAMF created the world’s largest Slack community for Mac admins.

The key is making these communities (whether a digital Slack community, a local meetup, or an annual conference) all about the job function or unique problem a group of people faces. Gainsight’s conference is all about customer success, not Gainsight.

The copycats can’t replicate this because a real community requires proving yourself year over year. You can’t just vibe code an app and get 10,000 people to join your Slack community. It’s about creating a place for real connections, and it has to come from authenticity.

2. Thought leadership

If I’m buying a product, I want to feel like I’m buying it from someone who sees the future of the space they’re in. Someone who’s an expert and has felt the pain. Someone who knows the problem better than I do and can help me get better at my job.

You can’t just show up one day and become a thought leader. You have to build credibility over time. And in a world where AI can generate content in seconds and everyone is just copying each other, real thought leadership is about taking the time to create something unique and helpful.

At BetterCloud, we put out a State of SaaS report every year for over a decade. It required collecting information from thousands of people, identifying the right questions to ask, and putting it all together in a consumable way. AI isn’t going to do that for you. I also wrote two books for IT leaders and we had a podcast featuring forward-thinking folks in the space.

It’s not that these things sold millions or had millions of subscribers. That’s not the point; the point is, the people who got value from these things are the exact people we wanted as customers.

Reputation and credibility take time to build. It’s not something someone can easily copy or pay to accelerate.

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3. Raving reviews and word of mouth

There could be ten products in your space that are literally the same thing on the surface. But as a buyer, how do I know what’s real and what’s a knockoff?

Third-party validation and social proof is how buyers know what’s quality and what will solve their problems. It’s customers who have used your product, saying it delivered the value it promised and it made a real difference to their company.

This shows up as customer reviews, case studies, and word of mouth. And you can’t shortcut those. Customers have to buy the product, use it, see results, and then you have to ask them for validation. That’s not something a copycat can fake in a couple of weeks.

One of the most impactful things I’ve seen is getting happy customers in the same room as prospects. This real-time interaction gets potential customers excited about your brand when they see energy in the room.

Bring a camera crew to your customer summit and record customer testimonials. Have your customer success team send a link to submit G2 reviews once they have validated that the customer is getting real value. Create a digital “wall of love” that consolidates all positive messages, reviews, and praise from your customers so prospects can see them. And showcase customer stories front and center on your website.

Positive word of mouth takes time to build, and copycat competitors can’t replicate that right out of the gate.

4. Partner networks

A partner network multiplies your reach in ways you can’t replicate by hiring.

At BetterCloud, I could only hire 20 salespeople because that was the budget. But if we worked with 20 partners, and each of those partners had 30 salespeople, we just expanded our network from 20 to 620. Imagine how many more people 600 people can talk to every day.

And those partners already have relationships with their customers. They’ve taken the time to build trust and community and thought leadership. Now you’re leveraging their trust that’s already there. You’re leveraging their distribution network.

Look at companies like Salesforce, ServiceNow, Workday, and Atlassian. Are they the best products? I don’t think so. But can anyone displace them quickly? No. Why? They’re protected by multiple layers of partners who are motivated to protect them because they’re profiting off the relationship. Microsoft says that for every dollar of ARR on their platform, partners make $10. What are those partners going to do to protect their $10? They’re going to defend Microsoft.

Partners come in different forms. There are enterprise partners like the Salesforce ecosystem or Atlassian marketplace, and distribution partners like Google Workspace working with domain registrars. When you buy a domain from GoDaddy, it asks if you want a Google Workspace account. With a good partner network, you’re not just creating distribution, you’re boxing out competitors.

5. Customer experience

Whether you’re buying something in the drive-thru at McDonald’s, changing your flight on Delta, or implementing the most complex, mission-critical platform at the core of your company, human beings recognize a good customer experience.

AI can handle a lot. Maybe 75% of frontline support questions. But what about the other 25%? When I call Delta and I’m stressed out trying to rebook my flight, speaking to a human being who can navigate me through that experience matters.

This is especially true for mission-critical software. BillTrust’s CEO Flint Lane personally called every one of his top 100 customers during a malware attack. At the time, Billtrust processed billions of dollars in payments each year.

That’s customer experience. It’s built on trust. And the copycats can’t easily copy it because it’s expensive and takes time.

Sure, using AI to solve routine requests can help a company cut costs. These savings on Customer Experience are one of the reasons a copycat can undercut you on price. But when someone buys a product for tens or hundreds of thousands of dollars, how you support them when things go wrong matters.

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6. Creative growth hacking and personalized outreach

Standing out from the crowd is hard. Everyone has access to the same tools and distribution channels. So what sets you apart is the creative, hard-to-scale GTM motions that require personalization, creativity, and effort.

I recently heard about a company that conducts deep research on a prospect, creates a custom whitepaper for them, and then puts it into NotebookLM to generate a podcast. They send the 10-minute podcast with the attached white paper to the prospect. It took a ton of time, but it worked.

I’ve worked with companies that sent their sales team to people’s offices with swag bags and handwritten notes. One salesperson who would buy golf trading cards and send them with handwritten letters to prospects. He’d write something like, “You remind me of Tiger Woods because of these things you did in your career, card enclosed.” His response rate was around 80%.

Once, someone cut out an article from the New York Times in which I was featured, framed it, and sent it to my office with a handwritten note explaining why the article resonated with him. How could I not respond to that?

These things build trust because they require time and real human effort. And while it’s possible to copy them, most companies won’t put in the work.

The foundation that makes it possible

None of these strategies work without a mission-driven team that actually cares.

You can’t build an authentic community with contractors who clock out at 5 pm. You can’t deliver exceptional customer experience with people who don’t care about the outcome. And you can’t create real thought leadership when your team is just going through the motions.

Building a company is difficult, no matter what technology exists. Going from zero to something is really hard. So is going from something to scale. It comes down to the people.

Choose the right people, motivate them, and give them a mission and values they actually want to live by. Show them the impact of their work, have them see how it’s helping customers, and make sure the customer is front and center.

If you do that, your team will go above and beyond because they care, not because they’re paid to. That’s what makes the difference and enables the above six strategies to happen.

Today’s moat is built on a foundation of trust

When all of this is done together in unison, it becomes part of your brand’s unique DNA, and it’s all centered around trust. It’s how people experience your company, how they talk about you, and what they associate you with.

When you do these things, it’s clear you’re not fly-by-night: you can actually hold the line on your price, build long-term relationships with your customers, and they will buy over and over again. But building that trust takes an incredible amount of work, care, and investment of time, money, and energy.

As Flint Lane said, a company is like a castle. But it’s more than just the castle that protects you. There are drawbridges, there are arrows, and there are multiple layers of protection. All these things together give you trust that your family will be safe when the inevitable enemies attack.

In the end, trust is the competitive moat around your fortress, and that’s how you win in an oversaturated market.

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What other CEOs say

Second-Mover Advantage
Max Junestrand, Co-founder and CEO of Legora, describes a strategy of competing with larger, better-funded rivals by capitalizing on second-mover advantages and disciplined product decisions. He highlights avoiding costly missteps, enabling faster iteration and better performance. Legora now competes head-to-head in major deals and is seeing exponential growth.

Mission as Moat
Ryan Wang, Co-founder and CEO of Assembled, focused on integrating AI with human support to differentiate themselves in a crowded field of support automation startups. He emphasizes that Assembled’s mission — helping companies scale high-quality customer support — resonates with both users and customers, offering a holistic approach combining AI and human empathy. This alignment of mission, product, data, and customer insight forms a compound moat.

Customer-First Product Vision
Phil Fernandez, Co-Founder & CEO of Marketo, describes a customer-first strategy that deliberately ignored competitors. He led product development without ever reviewing rival offerings, instead focusing entirely on solving customer problems and gathering feedback directly from users. Sales reps were trained to avoid competitive comparisons and instead reference satisfied customers to illustrate value.

Outlast, Not Outspend
Kyle Porter, Founder and former CEO of Salesloft, executed a competitive strategy focused on endurance, customer focus, and cultural values rather than feature battles. Despite facing better-funded rivals, Salesloft outlasted competitors and won through execution, innovation, and organizational health. Porter underscores the importance of deeply understanding and serving customers.

Customer-First Positioning
Ryan Westwood, Chairman and CEO of Fullcast, explains that their competitive edge lies in prioritizing RevOps leaders over sales leaders or reps, distinguishing their platform from legacy tools. He saw opportunity in disrupting incumbents ripe for replacement. Fullcast aims to scale by offering lightweight SaaS validated by market size and clear differentiation.

Speed and Autonomy Over Scale
Craig Walker, Founder and CEO of Dialpad, explains that he left Google to build a communications platform independently due to the speed and autonomy startups offer. He highlights the agility of a startups compared to larger, slow moving organizations where internal priorities often shift.

It’s December 18th, 2025. There are 13 days left in the year.

If you’re like most CEOs, you’ve been grinding for 11 months straight. Your team has been grinding with you. You’re trying to close deals, hit your goals for the year, and sprint across the finish line. You’re exhausted. Your team is exhausted. And the temptation right now is to just collapse into the holidays and be done with it.

But these final two weeks of the year are the perfect time for every leader to zoom out, examine what you’ve accomplished, celebrate those wins, and wind down intentionally so you’re ready for the year ahead.

Right now, before you take that much-needed holiday break, here are the three things every CEO should do:

Reflect. Rally. Recharge.

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Table of contents

1. Reflect: Look back on the year

2. Rally: Communicate wins to your team

3. Recharge: Use the world’s slowest week to truly rest

4. Close the year with intention

1. Reflect: Look back on the year

As CEOs and company leaders, we don’t take enough time to step back and see the progress we’ve made.

I’m as guilty of this as any CEO. When you’re heads-down grinding, you rarely pause, especially at year-end when you’re stressed and the holidays are coming. You just keep moving. And if you’re like most founders I talk to, you’re never satisfied. The goalposts are always moving, so you’re constantly chasing the next achievement.

Do not forget that even if you didn’t hit all your goals this year, you’ve made progress. Sometimes progress means just discovering what doesn’t work. If you’ve been hustling for 11 months with your team, you’ve moved forward in some way or another.

The end of the year is a forcing function for reflection. Use it. Take a few hours and write down what you’ve accomplished across three areas: your business, your team, and yourself.

Reflect on the business

Start with the quantitative stuff. How far have you come from a numbers perspective? Revenue, customers, money raised. Look at your KPIs: retention, product usage, NPS, and how many public testimonials you’ve collected. Write it all down.

Then, look at your qualitative progress. Did you ship features you’ve been working on for months? Do you have customer success stories where your product changed someone’s business? Did you land a key account? Is your brand more recognizable than it was in January? Did you establish or make progress on any partnerships or win any awards?

Reflect on the team

After that, look back on where your team was at the start of the year. Have you brought on A-players who took the business to another level? Have you removed people who were holding you back? Are your company values more celebrated and lived than they were at the start of the year?

Reflect on yourself

Finally, look inward. Did you become a better leader? Are you better at running board meetings? Better at your one-on-ones? Better at strategy and decision-making? Are you more recognized as a thought leader in your space? What were the gaps in your support system that you filled?

Why reflection matters

When you look back across 12 months, you see how far you’ve actually come. It’s like watching a child grow. As a parent, you don’t notice them getting taller day after day. But when you look at a picture from a year ago, you see that growth very clearly. You’re with your company every day, so you don’t see it. But step back and look where you were 12 months ago and you’ll see it was a different company.

It is important to reflect on the distance you’ve traveled in a year, and where your work actually paid off. That perspective gives you the energy to move forward, and the confidence to achieve even more in the year to come.

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2. Rally: Communicate wins to your team & investors

After you’ve reflected, it’s time to communicate what you’ve accomplished.

Your team and your investors need to hear from you. They need to be energized as they head into the new year.

And this moment, right before the holidays, is uniquely powerful. Christmas to New Year’s is the only week when almost the entire world shares a vacation. Everyone is in the same headspace: new year coming, time with family and friends, conversations about work and life.

If you can give people a rallying point at this moment, it’s incredibly powerful. People want to tell their families they work somewhere great. They want to tell their friends their company is doing well.

Rally your company

Write a year-end message to your team and send it to them by December 23rd. This takes time. I used to spend hours, sometimes days, writing this message at BetterCloud. It was a write-up reflecting on the entire year.

Here’s how to do it:

• Remind people what the company looked like on January 1st. It’s easy to forget. “We didn’t have this feature. We didn’t have that feature. Our team had this many people. Our customer base looked like this.”

• Then, fast forward 12 months and show them what’s changed. Include graphs with trendlines if you have them. Screenshots of the product before and after. Photos of the team at an offsite and at events with customers. Help them see that it’s a different company now. And it’s directly because of their hard work.

• Make it an exciting and high-energy message. This should help the team reflect but also drive excitement for what’s to come. “Going into next year, we’re stronger, better positioned, with a bigger opportunity ahead. Imagine what we can achieve.”

Post this everywhere your team communicates: email, Slack, Notion, your wiki. Make sure people see it.

Pro tip: Save this write-up in a private Google Doc for yourself. After 10 years at BetterCloud, I went back and read my first year-end message. It was wild. The first one talked about our first customer. It becomes a journal entry for your company, and I’m so glad I did that.

Loop in your investors

Most CEOs will send that message to their team and stop there. Don’t do that. Take the same message and forward it to your investors. Add some context if you want: final numbers, additional KPIs, lessons learned.

Your investors want to hear how you’re doing. They see the evolution even less than your team does. They sit on multiple boards, they’re busy, they’re not in the business every day.

When they get your message and see your authentic, transparent communication to your team, it goes a long way. They’ll think: “Wow, this company really did make progress. And the CEO is excited and thoughtful about where they’re going.”

Reach out directly to top performers

This is another part most CEOs skip. Don’t. The ROI of this is actually insane. You want to keep those top performers, and this gesture goes a long way.

Send personal messages to the people who really moved the needle this year. Not just your direct reports. Anyone in the company who made a real difference.

Call the top sales rep who closed those three big deals that changed your year. Call the engineer who worked weekends to ship that killer feature. Thank them specifically for what they did.

People want to be acknowledged. These messages matter more than you think. They’ll tell their families over the holidays, and they’ll remember it for years. And the next time they’re facing a big challenge, they’ll go the extra mile because they know you “see” them.

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3. Recharge: Use the world’s slowest week to truly rest

One of the most important pieces of a CEO’s support system is knowing when to rest.

Between Christmas and New Year’s, the world slows down. Email volume drops to the lowest it’s been all year. Most of your employees are on PTO. Your customers aren’t asking for help. There are fewer demands, fewer expectations, and fewer fires to put out.

This is the world’s downtime, and you need to leverage it to recharge just like everyone else.

As CEO, you won’t get a sabbatical when you’re burnt out. But here’s the thing: with just a few days of truly being off and disconnected from work, you can recharge a lot. Use the time between Christmas and New Year’s wisely, even if it means doing nothing at all.

This week is the most efficient time to recharge because you won’t be interrupted. You don’t have the fear that something important could be happening. It’s the holidays. Nothing is happening.

Do whatever recharges you. For me, it’s sitting on the couch watching random TV shows and drifting in and out of sleep. I rarely do that, but over the holidays, it’s what recharges me. For other people, it’s hiking in the wilderness. For some, it’s hanging out with family. For others, it’s specifically not hanging out with family.

Whatever truly recharges your battery, prioritize it for at least a few of these days.

The importance of recharging

Your company works off your rhythm. If you don’t recharge and you show up on January 2nd still feeling sluggish and needing rest, your entire company will follow suit. That’s not what you want.

Take the time now so that when you show up in the new year, everyone knows: “We’re back to work. We’re ready to go.” Make it clear to your team that you’re recharging. Make it clear to your family that you’re recharging. And then make it clear when you’re done recharging.

This is how you maximize every hour and every day of the year ahead. But you can only do that if you truly rest now.

Close the year with intention

This isn’t a fancy framework or a complicated planning session. It’s just three simple things: reflect, rally, recharge.

If you’re reading this on December 18th, you have 13 days left in the year. Use them intentionally. Reflect on how far you’ve come. Rally your team, your investors, and your top performers. And recharge during the only week when the entire world is doing the same thing.

These three actions will set the tone for the following year.

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Key takeaways

• Reflection gives you perspective on progress you can’t see day to day and provides the energy to move forward into the new year.

• Write a year-end message to rally your team no later than December 23rd, showing where you started versus where you are now.

• Forward that same message to your investors and send personal notes to top performers who moved the needle this year.

• The Christmas-to-New Year’s window is the only time the entire world shares a holiday, making it the most efficient week to recharge without interruption.

• Your company follows your rhythm, so make it clear when you’re recharging and when you’re back, so everyone starts 2025 ready to execute.

I was at a VC offsite hosted by Crosslink recently where they dedicated an entire session to AI in the enterprise.

The room was packed with founders comparing notes on how to land their first customers, integrate deeply enough to matter, and convert pilots to multimillion-dollar contracts. There were a lot of discussions on how to approach GTM, and the conversation kept circling back to one thing: forward deployed engineers (FDEs).

Everyone is talking about FDEs right now. Founders are actively hiring for these roles. VCs are pushing their portfolio companies to build FDE teams. But not everyone actually understands what a forward deployed engineer does, how to find qualified candidates, or how to structure the role so it actually works.

I’ve spent the last decade helping tech companies build their leadership teams at True Search. We’re the largest technology-focused executive search firm, and we’ve worked with companies like Twilio and Spotify since their earliest days. More recently, I’ve focused on AI-native startups, and I can confirm there is a shift in the types of roles these companies need to succeed.

I’ve placed several forward deployed engineering roles at various companies. What’s become clear to me is that FDEs are actually the key to whether these businesses will survive.

In this article, I’m going to explain what a forward deployed engineer is, why this role is more important than ever, what to look for when hiring an FDE, and share tips on compensation and org structure.

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Table of contents

1. What is a forward deployed engineer?

2. The importance of FDEs in the AI era

3. FDEs vs. other technical roles

4. The FDE profile: what to look for

5. How to find forward deployed engineers

6. FDE compensation structure

7. Where FDEs should sit in your org

What is a forward deployed engineer?

A forward deployed engineer is someone who lives at the intersection of customer needs and product development. They’re engineers dedicated to specific customers, building solutions on the fly that aren’t part of the core product yet. FDEs also close the loop with product teams to turn custom solutions into platform features.

Palantir is well known for introducing this model in the early 2010s with their “echo and delta” approach. They embedded engineers with customers to deploy and customize Palantir’s platforms, ultimately maximizing value and adoption. But the role is having a moment right now because the problem it solves has become critical for AI companies.

Renata Quintini at Renegade Partners recently shared this about the FDE role:

So, what do FDEs actually do?

• They spend time directly with a customer to understand their workflows, then build custom scripts, integrations, or features to make your product work for them.

• They introduce functionality that meets immediate customer needs, even if they’re not on your current roadmap.

• They identify patterns across customers and figure out what should be built into the core platform so you’re not rebuilding the same solution for every customer.

The importance of FDEs in the AI era

Partial usage is a death sentence for any product, but especially for an AI solution. For a product to have any kind of moat in the AI era, it needs to become deeply embedded with your customer’s team and workflows.

AI products are uniquely vulnerable to being replaced by a competitor who delivers more value faster. This is because with AI, there’s little technical differentiation between most products. Most are built on the same foundational models, and the underlying technology changes constantly. New competitors can spin up faster than ever. The company that wins isn’t necessarily the one with the best model (they all have access to the same foundational models); it’s the one that becomes indispensable, and gets woven into a customer’s data, processes, and daily workflows.

FDEs are critical in making that happen.

But to get an AI product adopted in day-to-day workflows, nearly all AI products need access to a company’s internal data; this goes well beyond traditional API integrations. “Ankle biter” features that unlock that marginal extra user, or which drive incremental usage, can no longer be delegated to your team’s engineering backlog; delivering on them today is now critical to whether that pilot becomes an enterprise deployment, and whether your solution is sticky and defensible when the next competitor comes calling.

AI companies, from their earliest days, must deliver on all of this while navigating security and compliance concerns. Traditional customer success and account management play important roles, as does your core engineering team, but they aren’t designed to handle this level of technical complexity or velocity of customer response.

This is where forward deployed engineers come in.

FDEs make the product work in ways that generic implementations can’t. And in doing so, they create the kind of lock-in that actually matters, not through contracts or switching costs, but through genuine value that’s woven into how a customer operates day to day.

FDEs are the difference between a $100k pilot that goes nowhere and a multi-million dollar contract.

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FDEs vs. other technical roles

Forward deployed engineers aren’t sales engineers who demo features and answer technical questions during the sales process. They’re not solutions architects who design implementations but don’t build them. They are not members of your core engineering team who pick up the next feature on the roadmap. And they’re not traditional implementation consultants who just execute runbooks.

FDEs work directly with customers. They do hands-on building. They write code. They prototype and iterate. And when something they build for one customer proves valuable, they work with the product team to integrate it into the platform so all customers can benefit.

The role is still taking shape, and it means different things at different companies. But the core remains consistent: FDEs are engineers who can operate in ambiguity, build quickly alongside customers, and translate field insights into product improvements.

The FDE profile: what to look for

The best FDEs share a lot of DNA with early-stage CTOs, engineers, and former founders, and that overlap reflects the reality of what the role demands. These roles are particularly hard to fill because they require a highly skilled engineer who’s also comfortable talking with customers and capable of strategic product thinking.

Unfortunately, there aren’t enough former Palantir FDEs to go around. You need to know where else to look and what actually makes a great FDE.

Technical capabilities

FDEs need to be highly skilled engineers who can build quickly. This isn’t a role for someone who needs a lot of hand-holding or structured processes. You’re looking for people who can operate as an army of one, writing code, debugging issues, prototyping solutions, and iterating without a formal product spec to guide them.

They need to be hands-on. Some senior engineers are great architects but haven’t written production code in years. FDEs can’t afford to be that far from hands-on work. They must be ready to build integrations, write scripts, and ship solutions directly to customers. If they can’t move fast on their own, the model breaks down.

Customer-facing abilities

Technical chops alone aren’t enough. FDEs need to be conversational with clients in a way that many engineers aren’t. They’re meeting with your customer champions, business and operations leaders, and end users. They need to ask good questions, understand what problems people are actually trying to solve, and clearly explain technical tradeoffs.

This also means having a product mindset with a customer-centric approach. The best FDEs don’t just build what they’re told to build. They push back when a request doesn’t make sense. They identify the real problem beneath the customer’s request. And they’re comfortable building solutions on-site, in real-time, with customers watching.

Strategic product thinking

Technical and customer-facing skills are must-haves, but what separates good FDEs from exceptional ones is the ability to think strategically. Any engineer can build custom solutions for individual customers. But the ability to identify patterns, assess what multiple customers need, and prioritize which should be productized (rather than rebuilt each time) is an entirely different skill.

The goal is to minimize last-mile customization. Every bespoke integration you build is technical debt, and every custom script needs to be maintained. FDEs who think strategically are constantly asking: “Should this be part of the core product?” They bring insights back to the engineering and product teams, advocating for features that will reduce the need for one-off work and help customers succeed faster.

This recursive feedback loop is what makes FDEs fundamentally different from traditional professional services. The patterns FDEs identify don’t just help one customer, they become critical parts of the overall product roadmap. This coupling between field work and product development is critical to how enterprise AI companies progress and ultimately win.

It’s also why organizational structure matters so much. FDEs need a direct line to product and engineering teams, not a long chain of command that slows down the feedback loop.

If this profile sounds demanding, it is. You’re looking for someone who can code like a senior engineer, communicate like a seasoned CSM, and think strategically like a product manager. That’s a rare combination, which is exactly why these roles are so hard to fill, and why getting them right matters.

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How to find forward deployed engineers

The good news is that FDEs exist. The bad news is they’re not easy to find, and they don’t always look like what you’d expect from a traditional engineering hire. Here are some tips for finding qualified candidates for an FDE role.

Start by looking at internal engineering talent

An obvious way to source FDEs is to look at your own engineering team. You probably have engineers who want more product orientation but don’t want to lose their technical skills. Maybe they’re interested in talking to customers but don’t want to move into product management or customer success. Or they’re drawn to the variety of working on different problems rather than diving deep into one area of the codebase.

These engineers can make excellent FDEs because they already understand your product and your technical stack. The learning curve is shorter, and they can start adding value immediately. The challenge is that you’re pulling strong engineers away from core product work, so you need to be intentional about when this makes sense.

Focus on candidates with early-stage startup experience

The best external candidates for an FDE role usually come from early-stage startups. Specifically, look for founding or early engineers who joined before structured product leadership was established.

Startup background matters because at early-stage companies, customer thinking is required just to survive. You don’t have the luxury of waiting for a product manager to write a spec. You’re often talking directly with customers, figuring out what they need, building quickly, and incorporating feedback into what you ship. You’re iterating without formal processes or safety nets, and that’s exactly what FDEs do.

Consider former founders

Technical founders who’ve been through the startup journey (whether it ended in an exit, a shutdown, or something in between) can make phenomenal FDEs. They’ve lived through a 0-to-1 build experience. They’re used to ambiguity and direct customer engagement. They don’t need their hand held. And they’re often looking for a role where they can still build and solve problems without the weight of running an entire company.

The ones who didn’t succeed can be particularly motivated. They have something to prove, they’ve learned expensive lessons about what works and what doesn’t, and they’re often hungry to apply that knowledge in a role where they can see immediate impact.

Tailor your interview process

You need someone technical to assess these candidates. FDEs are building real integrations and prototyping solutions. They need to be strong engineers. If you try to hire for this role without a technical evaluation, you’ll end up with people who can talk a good game but can’t execute when it matters.

The interview process should be centered on hands-on problem-solving. Here’s what I’ve seen work:

• Collaborative kickoff session: Walk through a realistic problem and let the candidate ask clarifying questions. You’ll get a strong sense of how they think strategically just from the quality of their questions and how they frame the problem.

• Take-home prototype: Give them a real coding assignment that feels like an actual FDE project, such as building a prototype.

• Solution presentation: Communication is critical in this role. They need to be able to explain solutions to both customers and internal teams.

• Peer references: Go beyond manager references. Peer feedback reveals how candidates operate solo on projects and the level of impact they truly had.

Don’t skip the technical assessment; it’s foundational to everything they’ll do.

Compensation structure

Here’s where things get tricky. FDEs don’t fit neatly into traditional engineering compensation models.

Why traditional engineering comp doesn’t work

Standard engineering comp is straightforward: base salary plus equity, maybe a small bonus tied to company performance. That works for engineers focused on building the core product. But FDEs need to be measured differently. Their success is tied directly to customer outcomes (whether integrations work, whether pilots convert to full contracts, and whether customers expand their usage).

The need for variable compensation

That means compensation needs to reflect those incentives. You want something closer to a sales compensation structure than traditional engineer comp. Base salary should still be competitive with what you’d pay a senior engineer, but you need variable compensation tied to the performance of the accounts they’re working on.

It could be tied to customer success metrics, like pilot-to-contract conversion rates, expansion revenue, or specific milestones, such as successful integrations or go-lives. The key is making sure FDEs have skin in the game when it comes to whether their customers succeed.

We’re still learning

I’ll be honest: there aren’t many established models for FDE compensation because the role itself is still relatively new. Most companies are experimenting, and what works at a 50-person startup might look different at a 500-person company.

The important thing is to avoid treating FDEs like standard engineers (or customer success managers) when it comes to comp. If you do, you’ll either underpay them for the value they create (and eventually lose them), or you’ll attract people who are more interested in the stability of pure engineering work than the customer-facing and strategic nature of the role.

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Where FDEs should sit in your org

There’s no single right answer here. Where FDEs report depends on your stage, structure, and your key business goals.

Product org: This is where most companies land, and for good reason. FDEs gather signals from the field. They understand customers’ needs, what’s blocking adoption, and what features would unlock value. If they report into product, that feedback loop is shorter.

Engineering org: This keeps FDEs closer to the technical team and leverages existing relationships. It works well if your FDEs are contributing directly to the core product codebase. The downside is that engineering organizations are optimized for building scalable systems, not moving fast on one-off customer-specific needs.

Customer success: This makes intuitive sense because FDEs work directly with customers. But CS organizations historically lack technical depth. If you go this route, you need a CS leader with a strong technical background who can hire, manage, and support engineers.

Separate function: At early-stage startups, one of the founders is most likely the first FDE. As you grow, and hire FDEs, they will probably still report to the founders. A separate function can work long-term, but for most early stage companies, this adds unnecessary complexity.

The biggest org design challenge is how they coordinate with customer success managers. Both roles are customer-facing, but CSMs focus on relationship management and retention while FDEs focus on technical integration and building solutions. Define those boundaries early, or you’ll end up with territorial conflicts and gaps in ownership.

FDEs are how enterprise AI companies win

If you’re building an enterprise AI company, forward deployed engineers aren’t optional. The stakes are straightforward: in a world where technical moats don’t exist and competitors can spin up overnight, deep integration into your customers’ operations is a must, and FDEs make that happen.

Getting this right requires rethinking how you hire, compensate, and structure technical roles. You need engineers who can code, sell, and think strategically. You need compensation models that reward customer success, not just lines of code. And you need organizational clarity about how FDEs work with product, engineering, and customer success teams.

Start building your FDE function now. The companies that figure this out early will have a meaningful advantage over those that treat it as an afterthought.

Key takeaways

• Forward deployed engineers (FDEs) are critical for enterprise AI companies to achieve deep customer integration and prevent churn.

• FDEs build custom solutions for customers on-site, then identify patterns that should become core product features.

• Look for candidates with early-stage startup experience, former founders, or internal engineers who want customer exposure.

• Compensation should go beyond traditional engineering comp and include variable pay tied to customer success metrics.