The four phases of CEO evolution: From player-coach to force multiplier

What got you here won’t get you there

Can you scale with your company?

This is the question that keeps many first-time founders up at night, and there’s no way to know the answer until you’re living it.

Think about watching any sport from the stands versus being on the field. You can study game film and learn the plays, but until you’re actually in the game, you’re just watching. You can’t replicate the speed, pressure, and split-second decisions from the sidelines.

Running a company is the same way. You don’t know what it’s like to run a 100-person company until you’re running one. You can read about it, talk to other CEOs, and study the playbooks, but until you’re on the court, you’re just watching from the sidelines.

After scaling BetterCloud from zero to 350+ employees over 10 years, and working alongside 20+ founders as an advisor, I’ve learned that becoming a better CEO as the company evolves means becoming an entirely different CEO at each growth stage.

More customers, more team members, more funding, more revenue? I had to reinvent myself. I needed new skills, my responsibilities changed, and my priorities shifted. Each phase felt like I was starting over.

This is a breakdown of the four phases a CEO goes through as their company scales.

Table of contents

1. Phase 1: The player-coach (1 - 25 people)

2. Phase 2: The frontline manager (25 - 100 people)

3. Phase 3: The context switcher (100 - 200 people)

4. Phase 4: The force multiplier (300 + people)

Phase 1: The player-coach (1-25 people)

From the beginning up to about 25 people, you’re a player-coach. You’re on the field with your team doing the same work they’re doing, but you also have the added responsibility of pointing everyone in the right direction.

• Who’s reporting to you: Individual contributors

• How far out you’re looking: A day, maybe a week at most

What you’re actually doing

I was the office manager ordering snacks in the early days of BetterCloud. I was also the salesperson who did demos and closed deals. And I was helping our marketing person write blog content the same day I was pitching investors and looking for office space.

One time, I had to go to the Apple Store and buy a laptop for someone starting the next day. I sent out offer letters, I assembled desks, and I responded to customer support tickets. I was constantly switching between all of these functions in the early days.

What you need to know

Most first-time founders have never managed large teams. What they have is experience in an individual function and a passion for solving the specific problem their company addresses. Developers love writing code, salespeople love closing deals, and product people love building.

When you’re a player-coach, you’re still doing the work you’re most excited about while also leading. If your background is in development, you’re writing code. If you came from a sales career, you’re closing deals.

But you’re also doing work you’ve never done before and probably don’t want to do. GTM founders are using tools like Lovable to build products. Engineering founders are figuring out early sales motions. Everyone’s doing a little bit of everything, whether they know how or not.

This phase feels natural because you’re running on adrenaline and you can see your impact immediately, whether that’s solving a customer’s problem, sending an offer letter, or closing a deal that keeps the lights on. But the context switching is constant and stressful. The hard part is knowing when to let go and move to the next phase of the CEO journey.

Phase 2: The frontline manager (25 - 100 people)

From about 25 to 100 people, you become a frontline manager. You’ve hired or promoted a leader for each of the different functions, although many of them are junior because you can’t afford senior leaders yet. But you at least have people who can take direction and execute.

This is also where imposter syndrome can start to feel strong, especially if you’ve never been responsible for leading a larger team or leading functions that you’re not an expert in.

• Who’s reporting to you: Up-and-coming leaders, usually early in their careers

• How far out you’re looking: The next couple of weeks, maybe the next couple of months

What you’re actually doing

I started doing regular one-on-ones in this phase. I was still interviewing for every function at the company. But instead of owning sales accounts, I was joining calls while someone else owned the relationship. Instead of writing blog content, I was brainstorming new ideas with our marketing person.

I was reviewing and prioritizing the product roadmap line by line and making decisions on software purchases. I was still the Google Apps admin and the sys admin for every platform the company used.

What you need to know

This is when you start to step back from doing the tactical work in functions you’re weakest in. You hire more people for those areas (although you’re still responsible for them).

What I did (and what I see most founders do) is hire more senior people for functions where you have less capability, like engineering or product. And then you hire up-and-comers in the areas where you have strength and passion, such as sales, marketing, or customer support.

You’re still very much in the weeds, but the people reporting to you can take what you decide and execute it. That’s the main shift in this phase.

Phase 3: The context switcher (100 - 200 people)

When your company is around 100 to 200 people, you start to see two types of leaders under you: some who need coaching and others who need autonomy.

The senior leaders are strategic and fully own their functions. The others who came up from within or were given a chance to punch above their weight may need a lot of day-to-day help. Being able to respond dynamically to each is the key.

• Who’s reporting to you: A mix of up-and-coming managers with more experienced leaders

• How far out you’re looking: The next couple of quarters or the rest of the year

What you’re actually doing

This is when I started working on annual planning. I was spending time with leaders on employee review and interviewing processes. And I was spending more time with investors between board meetings. I was also meeting with potential game-changing partners or acquirers and doing a lot more public speaking. Travel became very frequent.

The type of work changed, but more importantly, the type of conversation changed depending on who I was meeting with.

What you need to know

This was the most confusing phase for me. The conversation you have with a senior leader is completely different from the conversation you have with a more junior person. With the senior leader, you’re spending most of your time talking about what’s coming around the corner, not what happened yesterday or today. With the more junior leaders, you’re in the weeds on tactical things: team decisions, prioritization of initiatives, and how to handle specific situations.

The meeting dynamics are different, too. With senior leaders, it’s often just the two of you – they handle the communication to their teams. With junior leaders, it’s often them and their team. You’re there to support them when sharing big news or rolling out an important initiative. Some people told me I was too in the weeds. Others told me I was being too strategic. I was constantly context-switching, and it left me exhausted by the end of most days.

The key skill here is identifying the most critical things in the business. Every business at this stage has smoke everywhere, maybe even fires. You have to decide which fires to let burn and where you’re going to focus your energy. That’s the job here, and it’s hard.

Phase 4: The force multiplier (300+ people)

At 300+ people, you finally have a full executive team in place. These are leaders running entire functions with full teams beneath them. Your job becomes fundamentally different.

• Who’s reporting to you: Executive leaders running full teams

• How far out you’re looking: 12 - 24 months out

What you’re actually doing

This is when I started spending a lot of time on storytelling: sharing wins, repeating the mission, and making sure our values were being lived. I was doing more thought leadership, preparing keynotes for our customer conferences, and setting goals with the executive team (but I was relying on them to execute).

I was also prioritizing time with our best employees and recruiting game-changing executive leaders. I was having conversations with the next set of investors and potential partners. Travel got even more intense. I was probably spending more time with people outside of the company than inside it, and that was a big change.

What you need to know

In this phase, I didn’t know about every feature being released anymore. I didn’t know every prospect in the pipeline or which roles we had open. And I was no longer involved in every interview.

It was more difficult to see the impact I was making on a daily basis. But if I spent my time wisely, I could make a much bigger impact than in the previous phases. A keynote that hundreds of customers hear, or partnerships that double the business in two years, finding one great leader for a critical function… these are the things you focus on in this phase.

My primary job was to ensure the executive team worked well together as a high-performing team and that everyone operated in line with our vision.

So, can you scale with your company?

Yes, but only if you’re open to constantly reinventing your role as CEO.

And this is important: this evolution isn’t exclusive to CEOs. Any executive or manager overseeing large, growing teams goes through similar transformations as the company scales. The specifics might be different, but the fundamental challenge is the same: what got you here won’t get you there.

With all of this being said, different people will experience these changes at different times in the company’s growth, especially today with AI, where you can do more with a lot less. But the vast majority of CEOs go through this evolution in some form. It’s part of the natural progression and growth.

I’ve seen second-time successful founders try to skip straight to phase 3 or 4 and bring in seasoned executives right away. But more often than not, it fails. There’s real value in being in the weeds early. Your team sees you do all the jobs, you meet them at their level, and they watch you build a healthy foundation and mindset before hiring a bunch of senior executives to run things. That has a positive long-term impact on culture.

What I do know is that my role as CEO was constantly evolving. But here’s what didn’t change: the job was always about context switching: jumping between functions, shifting focus, interacting with different levels of the company. What changes is the nature of what you’re switching between.

The question isn’t whether you can scale with your company, it’s whether you’re willing to reinvent yourself each time the company demands it.