Lenny's Podcast: Product | Career | Growth

How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe)

February 2, 2023

AI Summary

5 min read

Eeke de Milliano, head of product at Retool and early PM at Stripe, discusses practices for sustaining innovation, balancing process with creativity, and structuring product teams. Drawing from experiences building Stripe Connect, Radar, and Retool's recent launches like Workflows, Mobile, and Database, she outlines decision-making frameworks, cultural tools, and tradeoffs observed at both companies.

Stripe's Culture and Decision-Making

Stripe emphasized rigorous first-principles thinking, cultivated through founder-led questioning, a strong writing culture, and hiring like-minded people. Operating principles like "think rigorously," "move with urgency and focus," "users first," and "micro-pessimists, macro-optimists" guided behavior. Decisions distinguished trapdoor (irreversible, e.g., titles) from reversible ones (e.g., pricing), enabling speed without overanalysis. Communication relied on memos and reviews, linking clear writing to clear thinking.

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What you'll learn

1 `* (00:13) **Process and innovation tension**`
2 `* (03:39) **Eeke's Stripe background and key products**`
3 `* (09:13) **PM philosophy at dev-focused companies**`
4 `* (12:23) **Stripe's unique culture and operating principles**`
5 `* (21:23) **Fostering innovation and big thinking**`
6 `* (32:28) **Retool's three major product launches**`
7 `* (38:00) **Right process by company stage**`

+ Full timestamped outline available in the app

Show Notes

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Eeke de Milliano is the Head of Product at Retool and a former product lead at Stripe. In this episode, we discuss how any team can become an innovation machine. We talk about how a culture of writing led to a team of rigorous thinkers at Stripe. We cover tactics to breed innovative teams that you can replicate at your own company: From embracing retrospectives to creating systems that give individuals the "permission to think big". Eeke shares her framework for prioritizing resources between core products, strategic initiatives, and big bets, and how it helped Retool launch three new products in a year. She also gives a comprehensive overview of the right level of process for companies of different sizes, and how to build a talent portfolio.

Find the full transcript here: https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big

Where to find Eeke de Milliano:

• Twitter: https://twitter.com/eekedm

• LinkedIn: https://www.linkedin.com/in/eeke-de-milliano-3b05a629/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

Referenced:

• Snir Kodesh on LinkedIn: https://www.linkedin.com/in/snirkodesh/

• Stripe: https://stripe.com/

• Stripe’s operating principles: https://stripe.com/jobs/culture

• Retool: https://retool.com/

• Brian Krausz on LinkedIn: https://www.linkedin.com/in/bkrausz/

• Retool Workflows: https://retool.com/products/workflows/

• Retool Mobile: