There's a sentence I wrote in an internal document in 2020 that I think about more than almost anything else I've written. "Many hands, without skill, do not deliver."
I was COO at TravelPerk. We had a 20-person HR team. They were hardworking, well-intentioned people who had built something from nothing. And I had to make the case, in writing, that the team wasn't fit for the company we needed to become.
The diagnosis was uncomfortable. The org was designed around functional silos (HR ops, L&D, recruiting, business partners) which optimised for functional excellence at the expense of speed. Each silo wanted to perfect their own craft, irrespective of whether the business needed it. Every exec had multiple touchpoints into HR and had to fight to get their needs heard. The person running payroll across four countries had never run payroll in one. Their boss couldn't help either. Decisions flowed up to people without answers, then out to external advisors who didn't understand our context. Slow, expensive, and riddled with errors every single month.
The mission statement was the giveaway. "We create a unique journey for people to grow with TravelPerk." Lovely words. Makes the HR team feel warm inside. But the implicit prioritisation was individual first, team second, company third. The exact opposite of what a scaling company needs. When you're growing that fast, the lens has to be company first, team second, self third. Not because you don't care about individuals (you care deeply). But because organisational decisions made through the lens of individual comfort will slowly kill the company that employs everyone.
So we gutted it. Renamed it People Operations to make the change tangible. Rebuilt around a different set of principles: fewer people, higher talent density, squad-like structures instead of silos, self-sufficiently skilled individuals who could be grouped and regrouped as business needs changed. We kept the core of talented people and doubled down on them. We let go of the rest. I wrote the comms. I delivered them.
The hardest part wasn't the restructuring. It was the acknowledgement. These people had built something. They'd got us to where we were. And the honest answer was that what they'd built, and who they were, wasn't what would get us further. Honouring the contribution while being clear-eyed about the capability gap... that's the leadership moment nobody prepares you for.
I've now made some version of this decision three times.
At TravelPerk, it was a function. The HR team that got us to 400 people couldn't get us to 1,000. At Oliva Health, it was the product itself. We found PMF in workplace mental health, scaled past $3M ARR, diversified into leadership coaching. All of it worked. But coaching isn't a tech business. You can't have global impact through a model that doesn't scale. The thing we'd built, the thing that was working, wasn't the thing that would get us where we wanted to go. So we pivoted.
At readywhen.ai, it's the inverse. We're building with these principles from day one because we've already paid the cost of not having them. Small team, high talent density, no functional silos, company-first decision-making baked into the culture before there's a culture to retrofit. The people building readywhen.ai are the same people who went through both of those transitions. They already know what "what got us here won't get us there" feels like, because they've lived it.
The pattern I keep seeing (in my own companies and in every scaling company I've worked with) is that the moment you most need to make this call is the moment it feels least justified. Things are working. Revenue is growing. The team is trying hard. And that's exactly when you have to ask: is this the team, the structure, the product, the model that gets us to the next stage? Because if the answer is no, every quarter you wait makes the eventual change harder and more painful.
I'll leave you with Drucker: "The greatest danger in times of turbulence is not the turbulence. It is to act with yesterday's logic."
Yesterday's logic got you here. It won't get you there.