Executive hiring is one of those rare decisions that can bend a company’s trajectory. In my role leading product management at a high-growth SaaS company, I’ve seen the difference between a leader who compounds value and one who quietly drains momentum. That’s why I was eager to examine what actually makes (or breaks) these bets, and to share a practical lens you can use to improve executive hiring outcomes.
I sat down with Eeke de Milliano for a focused conversation on the realities of executive hiring, leadership transitions, and measuring success. We dig into the “buy or build a leader” decision, how to avoid common red flags, and what it takes to set executives up to thrive in hyper-growth environments.
Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company’s product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.
In today’s episode, we discuss how to rigorously assess executive hiring fit, including the challenges companies face when hiring new executives and the most common red flags and pitfalls I see teams miss under time pressure. We also explore practical advice for measuring success, especially when outcomes vs output get muddled in the first 90–180 days.
A recurring theme for me is that learning your own strengths is an underrated piece of the process. If you don’t understand the leadership leverage you already have on the team, you’ll over-hire for breadth or under-hire for depth. Great executive hiring clarifies the complementary edge you need—then measures it.
On the buy vs build decision: early signals matter. If you’re “buying” an external leader, pre-align on scope, authority, and what great looks like before day one. If you’re “building” from within, design a clear on-ramp and operating cadence so the leader can scale without drowning. In both cases, my mental model is to instrument leading indicators (team health, decision velocity, stakeholder trust) well before lagging business metrics fully show up.
Two red flags I always watch for: first, leaders who default to playbooks without interrogating context; second, leaders who cannot articulate how they measure success beyond activity and output. In hyper-growth, pattern-matching is useful—but uncalibrated pattern-matching is dangerous.
The human dynamics matter just as much as the strategy. What creates dysfunctional exec relationships is often misaligned interfaces: unclear decision rights, overlapping charters, or incentives that reward local maxima. High-functioning executive teams are like parents—a united front in public, with candid debate in private, anchored to shared principles and measurable outcomes.
Referenced:
ASML: https://www.asml.com/en
Claire Hughes Johnson: https://www.linkedin.com/in/claire-hughes-johnson-7058/
Constellate: https://constellate.team/
John Collison: https://www.linkedin.com/in/johnbcollison/
Mike Maples Jr.: https://www.linkedin.com/in/maples/
Patrick Collison: https://www.linkedin.com/in/patrickcollison/
Retool: https://retool.com/
Stripe: https://stripe.com/
Will Gaybrik: https://www.linkedin.com/in/william-gaybrick-5730347/
Where to find Eeke:
LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/
Timestamps:
(00:00) Should you ‘buy or build’ a leader
(03:45) Why do executive hires fail so often?
(09:35) Why the stakes are so high for leadership hires
(12:26) The hardest document Eeke ever wrote
(14:06) Two red flags in a new hire
(17:27) An example of an outstanding leader
(21:40) What creates dysfunctional exec relationships
(22:38) The three steps towards hiring successful leaders
(30:30) What you should know about outside hires
(33:12) Eeke’s advice for easing leadership transitions
(42:06) How to notice success patterns
(47:21) Why high-functioning executive teams are like parents
(52:02) The most surprising lesson from Eeke’s first stint at Stripe
(55:11) The leadership data Eeke wishes we had
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