Every so often a founder calls me with a version of the same worry. They’ve heard the stories about founders who “couldn’t scale,” and they’re starting to wonder if they’re about to become one. Sometimes they got there on their own. More often the board or their investors planted the seed and nudged them toward the conversation.
Here’s what I tell them: I think that narrative is mostly wrong. Most founders can make this transition. It’s a set of skills, not a personality type you’re either born with or you’re not. What’s true is that nobody hands you those skills, and the ones that got you here quietly start working against you.
I’ve been the “professional CEO” four times — the person brought in when a founder either chooses not to make the leap to scaleup leadership, or tries and struggles. Founders reach out to me because of it, and I’ve noticed I end up sharing the same handful of concepts every time. That’s what this is: the scaffolding I keep drawing on the whiteboard for how a scaleup CEO actually operates, written down.
Scaling isn’t a mystery to me — it’s been the core of my career. I grew lines of business as a product manager before I ran anything, then spent years as a CEO taking companies through exactly this phase. Most recently I helped take UserTesting from a fast-growing startup to an IPO, and then to a billion-dollar-plus acquisition and merger with the second-largest player in the space. It’s a hard stretch of road. It’s also a learnable one.
The inflection point looks like this. You’ve got some real product-market fit, a bit of repeatability, a hint of momentum. And then, usually somewhere between $10M and $20M in revenue, things stall. Growth slows, operational cracks show up, and the founder who seemed unstoppable a year ago suddenly feels out of their depth. Nothing broke. What happened is that the job changed underneath you, and no one announced it.
The founder job is to build a great product. The CEO job is to build a great organization that can deliver that product’s value to customers, over and over, without you in the room for every decision. Those are different jobs. You feel the seam right around Dunbar’s Number — the old idea that a person can hold about 150 relationships in their head before it stops working. Under that, you can run the company by knowing everyone and being in everything. Over it, you can’t, and every instinct that says “I’ll just handle it myself” now costs you more than it saves.
This series is about the gritty part of that transition. Not the coaching part — plenty of good people will help you with your presence, your communication, your work-life balance, and that matters. It’s just not what I’m useful for. I’m useful on the scaffolding: the systems, the operating rhythm, the frameworks for getting an organization that’s outgrown your own head to reliably do the things you’ve decided need doing. The stuff that, done right, is the difference between a company that scales and the corporate BS that founders start companies to get away from.
I’ve spent more than twenty years in enterprise software watching this play out — sometimes well, sometimes not. The failures are rarely about strategy. They’re about the mechanics nobody teaches you. So that’s where we’ll start: with the mechanics.
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