You just landed a big hire. Impressive resume. VP of Product at a Fortune 500. Led teams of 40. Managed a portfolio worth nine figures. They interviewed great, said all the right things about wanting to "get back to building," and now they're yours.

Give it four months.

I've watched this play out more times than I can count, and it almost always ends the same way. The impressive hire flames out, the founder is back to square one (minus six months and a pile of cash), and the company is worse off than before because now everyone's demoralized.

When I was at Suzy, we hired two product executives at roughly the same time. One came from a large enterprise company—the kind of place with formal processes, experienced teams, and org charts that actually meant something. The other was a senior director I'd worked with before and brought over because I knew he could operate in chaos.

Here's the thing about the senior director: he'd never been a director before. He'd been an IC his whole career, with maybe one brief stint managing a single person as a group PM. On paper, the enterprise exec had the leadership track record. My guy had almost none.

The enterprise exec was my peer. He lasted about five months before they let him go and gave me both roles.

Subscribe to keep reading

This content is free, but you must be subscribed to The Next Gear to continue reading.

Already a subscriber?Sign in.Not now

Keep Reading