What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)

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: Eeke’s wealth of experience as an executive leader The challenges companies face when hiring new executives Common hiring red flags and pitfalls Practical advice for measuring success Why learning your strengths is an underrated piece of the process – 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/ – Where to find Brett: LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/ Twitter/X: https://twitter.com/brettberson – Where to find First Round Capital: Website: https://firstround.com/ First Round Review: https://review.firstround.com/ Twitter/X: https://twitter.com/firstround YouTube: https://www.youtube.com/@FirstRoundCapital This podcast on all platforms: https://review.firstround.com/podcast – 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