Eeke de Milliano
Head of Product at Retool
Head of Product at Retool and one of Stripe's earliest PMs, where she helped build foundational products including Stripe Connect, Stripe Radar, Stripe Checkout, and Stripe Chargeback Protection.
Dimension Profile
Key Themes
Episode Summary
Eeke de Milliano shares deep insights from being one of Stripe's earliest employees and PMs, revealing the cultural mechanics that made Stripe exceptional: rigorous first-principles thinking, a strong writing culture, and the discipline to distinguish trapdoor from reversible decisions. She explores the fundamental tension between process and innovation as companies scale, and offers practical advice on when companies actually need PMs and how to build a talent portfolio.
Leadership Principles
- → Process is variance-reducing by definition — it brings low performers up but also brings high performers down
- → You can't be a good writer unless you're a clear thinker — writing culture drives better decisions
- → Most decisions are not trapdoor decisions — pricing, for example, can be changed more easily than people think
Notable Quotes
"Process, by definition, is variance reducing. You're bringing folks up to the average, but you're also bringing other folks down to the average. And oftentimes, the folks you're bringing down are your highest performers."
— On the fundamental tension between process and innovation in growing organizations
"I don't think you can be a good writer, unless you're a clear thinker. And if you couldn't write well, it was actually pretty hard to be successful at Stripe."
— On Stripe's writing culture as a mechanism for cultivating rigorous thinking
"No one would ever say, 'It's a best practice to do X.' People would be like, 'Well, why?' You had to go a few levels deeper."
— On Stripe's culture of first-principles thinking and rejecting conventional wisdom
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