EDITORIAL
The five hires you regret not making. The ones you wish you hadn’t.
A decade of early-stage founder interviews says the same thing: the wrong first-ten hires cost more than the wrong first product.
The Editors · 22 April 2026
Founders rarely talk about hiring the way they talk about product. Product gets a postmortem; hiring gets a silence. But the hire you made in year one is walking around in year five whether you like them or not.
Across a few dozen interviews with founders who grew past 50 people in the last decade, a pattern holds.
The hires you regret not making share a shape: slightly too senior for where you were, at exactly the moment you needed them.
The ones you wish you’d made earlier:
A full-time finance person, not a fractional CFO, before Series A. Every founder who waited past ten people wishes they hadn’t. You stop making pricing calls by vibe.
A real head of engineering — not the best engineer promoted — by the time you cross twenty-five. The best engineer is precious; the best engineer as a manager is the fastest way to lose them and slow the team at once.
A recruiter on payroll, not a contract, by the time you need your twentieth person. Not because contractors are bad, but because an in-house recruiter builds the muscle of selling the mission. That’s the muscle you’ll need for every hire after.
A second person in customer-facing work, not just a VP of sales, at $1M ARR. The best VPs of sales want a bench. You’re the bench until you hire one.
A trusted operator chief of staff, by year three at the latest, if you’re still the one scheduling your own week. They cost less than you think. They return more than you measure.
The ones founders quietly regret:
The senior hire from a Big Co who couldn’t work small. The title felt like a flex. Six months in, they’re waiting for decisions to be made by someone else.
The friend-of-a-friend early engineer who was a 7/10 the day they joined and never hit 8. In a seven-person team, the floor is everyone.
The first VP hire before there was a team to VP. Management is a solution to a scale problem, not a substitute for one.
What ties the pattern together: the ones you regret not making share a shape — slightly too senior for where you were, slightly too expensive for the week you interviewed them. The ones you regret making share a shape too — slightly too junior for the job, slightly too junior for who you were when you hired them.
The first list is a lesson. The second is a mirror.
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