The lure of freemium (like The Force) is strong. No headaches. Customers try and buy all on their own. Like magic.
The appeal of No Salespeople can be strong.
And freemium is certainly back in the Age of AI. ChatGPT, Claude, Cursor, Canva and more have all created incredibly powerful freemium offerings. Freemium is back in force. It never went away, but it’s back stronger than ever.
So No Salespeople can work. For a while. Maybe even forever, if you don’t want to build something really big. But to Go Big, almost everyone in SaaS at least eventually adds a sales team.
And yes, new AI sales tools will let us at least for SMB sales have fewer, better sellers. And in some cases, AI will likely be able to sell simpler products … on its own:
Yes, Twilio started off as self-service. But to scale, it quickly added a very effective sales team. Our deep dive with founder Jeff Lawson here:
Yes, Atlassian for a long time had almost no “direct” sales team, well after the IPO. But it always had a very large channel (i.e., resellers) that sold its product into the enterprise, and a lot of internal resources that supported the channel.
Those channel salespeople aren’t employees, so yes, leaning so heavily on the channel is less common. But it’s just third-party selling instead of first-party.
Much more in our deep dive with former CRO Cameron Deatsch here:
Yes, Windsurf is one of the hottest dev tools out there. But part of its secret sauce … was building an epic enterprise sales team. Even if the product at its core is totally self-serve:
And today, many of its products are now supported by an internal sales team, albeit one that doesn’t discount and more supports deals than negotiates them:
Monday.com stayed self-service for the most part — up to $30m-$40m ARR. But after that, the sales and success team fueled faster growth and much, much higher NRR to $240m ARR and beyond. More on that here.
See Notion above as another fun example. Or Open AI.
Stripe was self-serve for years, and very SMB. But … here’s our deep dive with Stripe’s CBO on how they … eventually … went enterprise and built out a full “traditional” sales team. Eventually:
Slack started off with no “outside” sales team. But it too, as it went more and more enterprise, staffed up with a deep and strong one as they crossed $50m ARR.
Fast forward to its IPO … and the majority of Slack’s growth was in the enterprise. In big deals. With, and through, a sales team. More on that here:
Box’s revenues are now ~90% through the sales team, from 0–1% when it started as a pure freemium product (more on that here):
What’s also clear here is you don’t need 100% sales-driven revenue to Go Big. “Hybrid” self-serve + sales models can be great for many SaaS and Cloud leaders. The power of PLG is real, especially when combined at scale with sales-led growth.
Today, many of Twilio’s bigger customers go through sales, but then a huge amount of the downstream revenue is “automatic” as customers use more. Hence, Twilio has a very high level of sales efficiency (and a relatively small headcount). But there’s still a real sales team there. They just only need to directly touch a subset of the total revenue.
It’s just hard to get past $100m ARR without going upmarket a bit, and closing larger deals. Calendly added its first real enterprise sales team around $50m ARR. You might be able to go even further. Canva waited until almost $1B ARR, maybe longer.
But it’s the law of large numbers that pushes you to go into bigger and bigger deals. And larger deals require a human touch. That can be done without sales. But if it’s only done with support and Happiness Officers … you close less revenue. More on the math here: Why You Need 50 Million Active Users for Freemium to Actually Work and why salespeople increase revenue here: Curse of the ‘Middlers’: Why Happiness Officers Can’t Stand In for True Sales Professionals
So convergent evolution says anyone trying to cross $100m in ARR or so will eventually add a true sales team. Maybe on Day 0. Maybe on Day 3650. Maybe at $30m-$40m like Monday.com.
Just don’t be totally against it.
And if you don’t think you need a sales team now, well great. It’s cheaper without one, no doubt. Just be on the lookout for the moment … when that changes.
