In this conversation, Peeyush Upadhyay, Managing Partner at Pekamiar, sits down with Jen Holmstrom, Partner at Notable Capital.

Jen explains why a company reaching $150 million in revenue with 28 people is no longer innovative, just the expectation. Why an executive who asks how big a team they can build will not make it very far in a hiring process. Why she thinks the one-person unicorn is not hype but probable, and why the code gen tools are still not replacing great engineers.

She breaks down what happens to leadership when teams get this lean, why a leader running twenty-two one-on-ones a week has a problem, and why, with all the innovation, companies still need management. She walks through the roles gaining power, from forward-deployed engineers and the office of the CEO to GTM engineers and a RevOps function that is merging with them.

On compensation, she is candid about how equity is being rewritten, including a 7% grant to a Series B head of engineering who was not even the CTO, and two-year vesting used just to get talent in the door.

Her answer to what separates the best founders is talent on offense. Repeat founders carry the battle scars of a bad hire, and they go out and meet great people long before they need them.

She also gets into the lesson Meta taught her about what really matters on day one, why you hire for where the company is going rather than where it is, what she saw in the founders of Handshake and HashiCorp, and why recent grads had better arrive with their AI skills ready for a bit of reverse mentorship.

This episode is part of our series on The Scaleup Flight featuring the Talent Leaders inside VC funds. The people who watch hiring play out across an entire portfolio, and whose knowledge almost never gets written down anywhere.

00:00 Highlights

01:32 Meet Jen Holmstrom

06:10 Lessons from search, Meta and venture

12:13 Is the one-person unicorn real?

14:20 $150 million with 28 people

15:46 What happens to leadership in lean teams

22:02 The rising roles: FDEs, GTM engineers and RevOps

30:12 Equity, comp and the 7% grant

38:03 Talent on offense: what repeat founders do differently

42:51 Why executive hires break

48:22 What Jen saw in the founders of Handshake and HashiCorp

55:49 Rapid fire

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