I get 50+ cold emails a day. Most of them are garbage: AI SDRs congratulating me on things I didn’t do, personalizing to a company where I don’t work, and even pitching me a product that competes with my own.
That said, I still close deals from cold outbound. I also occasionally take meetings from cold pitches. I know it works because I’m both selling and buying through it.
But cold outreach doesn’t work the way it used to. For the companies that understand what’s changed and are willing to put in the work, it can still be a key part of your company’s sales and marketing strategy. But it can’t be the only thing you lean on, and (even with AI), it’s not going to run on autopilot.
Key takeaways
Cold outreach still works, but it’s changed. Volume no longer wins. Precise targeting, deliverability, and human judgment do.
Personalization at scale doesn’t work. It triggers spam filters, and it looks robotic.
Don’t overlook deliverability. Keep your lists clean, warm up your domains, monitor bounce rates, and use secondary domains when testing.
Humans have to stay in the loop. AI can handle the grunt work, but choosing who to reach, when, and what to offer requires human judgment.
Table of contents
Why cold outreach broke
The modern cold outreach playbook
Outbound for low AVC vs high AVC products
The role of humans in cold outreach
Why cold outreach broke
Cold email was getting harder well before AI, but AI slop made the situation untenable. Rookie SDRs with ChatGPT, desperate marketers armed with AI SDR platforms, and offshore agencies all flooded inboxes with horribly written emails.
It’s an arms race, and the email providers have AI too. They started fighting back aggressively. There are three general ways they detect spam.
First, they look at the technical configuration, including sender reputation, domain reputation, and the history of the email account itself. Get this wrong, and you’re instantly in the spam penalty box. It doesn’t take a PhD to recognize that sending 100 emails a day from a brand-new email account is suspicious.
Second, they look at the content itself. If it resembles other content that people labeled as spam, it goes to spam – and nobody ever sees it. Sometimes it might end up in another version of the penalty box, like “mailings,” or “newsletters,” or some other folder that nobody ever looks at, but for the salesperson, that’s still a miss.
Finally, the email providers leverage the network effects of operating at a massive scale: they see all the emails and can spot patterns such as the timing of sending, the overall activity of an email account, and more. Companies maintain domain blacklists and share them with others. Once you are presumed to be a spammer, it is very hard, expensive, and time-consuming to recover.
Tip: A telltale sign that your emails are landing in spam is that you never get any replies. If you didn’t even get an out-of-office response, your campaign likely landed in spam.
The good news is that you can fix that by following this playbook.
The modern cold outreach playbook
Five years ago, cold outreach could drive your entire pipeline. Those days are over. But cold outreach has a place in most B2B sales processes because it remains extremely cost-effective and can drive both top-of-funnel and bottom-of-funnel success.
Success with cold outreach means not only being good at email but also combining it in a broader GTM context. Here’s where to focus.
1. Deliverability (getting the tech right)
Deliverability is the most important aspect of any cold outreach strategy. If your email is not delivered, you have accomplished nothing. Managing deliverability is a full-time job because it’s always changing. Google and Microsoft are finding new ways to make life difficult for salespeople. You can either outsource this or have your salespeople fight this battle themselves.
If you’re fighting this battle yourself, make sure to set up secondary domains, properly warm up emails, limit your sending volume, and monitor the health of everything. You have to configure all of that correctly and test it. No shortcuts, or you will land in spam.
Your content matters to deliverability, so don’t expect your first few campaigns to succeed. Instead, find a balance that both gets delivered and drives engagement from your prospects.
While deliverability is the most important factor, it is not the only thing that matters for success. You still need to come up with copy and subject lines that people react to and engage with.
2. Warm up your audience with layered campaigns
One way to improve engagement is to layer your campaigns. This reflects how humans actually engage with emails from a stranger.
For example, start with an email that doesn’t ask for anything. No links (to avoid spam filters and preserve deliverability). Even if you want them to click a calendar link and book a meeting, the first email is the wrong place. Send the meeting request later in the sequence, or respond to a reply with your booking link (a pro move).
The companies closing deals from cold outreach are running 5-7-touch sequences over 3-4 weeks. Some do as many as 19 touches across multiple channels and campaigns (email, phone, LinkedIn, or other social networks) – but that’s rare.
3. Focus on quality, not quantity
If you’re selling something to a massive market, like accounting software or broadband internet for SMBs, you can send 100,000 or 1mm emails a month and hope a few people become customers. This can still work (I’ve seen it). But it’s extremely expensive to send that many emails (we’ll get into why later).
For everyone else, especially high ACV sales, figuring out what makes a quality prospect and how to reach them at the right time always beats volume. A targeted list of 50 or 100 companies will beat a spray-and-pray 5,000 contact campaign every time.
The quality of the list usually leads to higher quality everything else: subject line, messaging, and call to action. Because if you put in the work to narrow your target, you’ll know what they care about and what to say that will resonate.
4. Leverage live events
No single tactic performs better for more companies than outreach related to a conference or other live event. These campaigns are urgent by nature. People who go to conferences are usually there because they are in the market for products or services, and they have more time to meet because they blocked their calendars for the event.
It depends on your industry, but generally speaking, this is what works:
Book meetings at the conference before you go. Do this by getting the attendee list beforehand and sending emails 2-3 weeks prior (not earlier than that, people won’t be thinking about the conference yet).
Then, follow up with the people you met, and even with those you didn’t (“Sorry I missed you…”). Both can be automated with the right AI tools. Email them afterward with something specific from the event. Just attending the event makes you much more credible than 99% of the other people using email to try to get their attention.
Obviously, this works better for high ACV sales (where people are going to conferences to look at solutions) than for low ACV, mass-market sales (where timing matters less and it’s a volume game).
5. Get creative
If you’re not reaching your targets directly, it’s time to try a different tactic. Reach out to influencers they already listen to. Connect with their advisors, board, or investors. Be a guest on a podcast they listen to (cold outreach to podcasters works well because they need guests on their shows). These people may be more open to hearing you out and can turn into a warm intro.
Fractional advisors or consultants are always looking for new products and services to recommend to their clients, and staying on top of the latest tech signals expertise.
The cycle might take longer from conversation to new customer, but if you can turn one conversation into multiple customers, that’s a huge win.
6. Be strategic with multichannel
Cold outreach performs best as part of a multichannel strategy. Email plus LinkedIn. Email plus cold calls. LinkedIn plus cold call. LinkedIn ads or retargeting. Cold email invites to an exclusive dinner (yes, this works). Pick at least two channels and make sure they reinforce each other.
For example, Jason Lemkin from SaaStr uses agents to automatically email visitors to their website. This is known as “warm outbound”. This is a very popular play and extremely effective–but you need a lot of website visitors for it to lead to deals. It pairs well with SEO or SEM.
Outbound for low ACV vs high ACV products
The tactics and tools for low ACV products are different from those for high ACV products, because the economics don’t justify the kind of thoughtfulness, research, and funnel that a larger sale would.
Outbound for low ACV
For products under around $50k per year, the sale might be more transactional, especially in large markets. Above that, you are targeting smaller markets and usually running a salesperson-driven sales process.
The focus for low ACV products is volume. It’s not worth the effort or expense to figure out who is in the market right this second. Instead, cast a wider net. Companies doing low ACV cold outreach succeed by sending 100k or even 1mm emails a month.
To do that, they use tools like Instantly, which provide very low-cost sending infrastructure. This is a volume game and should be treated as such – you’re going for CPMs (Cost Per Thousand Impressions). So if you send 100,000 emails and get a 40% open rate, that’s 40,000 impressions. If that costs you $10,000, that’s a $250 CPM. That’s a worthwhile investment for many companies.
Outbound for high ACV
If your average deal size is $50,000 or more, cold outreach works differently. The tooling is also different. You need precision, not volume.
Doing cold outbound by hand used to be viable, but today, with cold outreach success rates dropping and the complexity of deliverability increasing, the math doesn’t work without help from technology. This is where the right AI products shine.
Instantly and tools like Salesloft, Outreach, or Unify all have steep learning curves and take time to use. Moreover, they’re based on templates and predefined workflows, so they lack flexibility, and every campaign requires extensive configuration work and ongoing monitoring. Other products, such as Skyp, the company I founded, are built specifically for sales outreach to high ACV prospects.
Small, targeted campaigns to 15-30 people work better than templated blasts, and we help make the entire process manageable, enabling SDRs and AEs to run focused micro-campaigns without wrestling complex interfaces.
The role of humans in AI cold outreach
AI outreach has gotten a bad rep, for good reason, but leveraging AI as part of your outreach strategy can still make sense. The key is making sure humans are still involved where necessary. There are three areas where humans have a huge impact.
1. Choosing the right people to reach. One CEO I spoke with sells at a minimum of $200k, and has 50k possible buyers. Others might have as few as 2,000. Humans need to be involved in figuring out who to reach out to. Not building the lists by hand, but directing the AI and reviewing its work. For ABM motions, you can still use AI, but you have to be extra careful in choosing who you reach out to.
2. Timing. Humans know what’s going on in a market. Did Mythos change how CISOs work? Is the Iran war causing havoc? Did that hire mean a prospect is likely to be in the market? You can (and should) automate finding and enriching contacts, but choosing when you send and what you talk about – let a human do that.
3. Choosing your offer. An offer is what you present to the prospect at the end of your email – maybe it’s a webinar, or a whitepaper, or a spot at a golf event. Salespeople talk to customers all the time and therefore understand their preferences and constraints. They know whether a busy VP wants a 30-minute call or a whitepaper they can read on their commute home. AI can’t make those calls.
4. Cold calling. The AI bots haven’t come for the cold callers – yet. Only because they’re not allowed to. Using AI for cold calling is currently illegal.
This leaves most of the actual grunt work – managing deliverability, uploading lists, setting the cadence, writing the emails – to AI, which opens new opportunities. For example, AI can learn from each message and campaign, and improve without human input. It just requires some up-front input and oversight from humans.
Using legacy tools requires humans to continually focus on rote aspects that add far less value. Why check your blacklist status weekly when an AI can check automatically every day?
Build the right cold outreach process for your business
The winning strategy is to tailor your outbound process for your own business. You can’t cut and paste someone else’s process and get the same results.
It takes real work and the right tools. The winning companies are using AI to scale the right parts and keep human judgment where it matters. They’re combining email with other channels. They’re targeting narrow lists with high relevance and deep personalization rather than blasting everyone.
Cold outreach still works, but only if you do it right. That means protecting your deliverability, being thoughtful about who you email, and using personalization for good effect. It means running multichannel campaigns and respecting the fact that the inbox is crowded.
FAQs
Does cold outreach still work?
Yes, just not the way it used to. Inboxes are more crowded, and spam filters are stricter. You need to target the right people and protect your deliverability.
How do I avoid spam filters?
Clean your lists regularly and warm up new domains. Don’t send from your primary domain when testing something new.
Should I personalize emails or use templates?
This one’s tricky. Templates get spotted quickly, and too much personalization triggers spam filters. You need to show them you understand their business, not that you stalked their socials.
