Jeff Weinstein

Product Lead at Stripe

Product lead at Stripe who scaled payments to hundreds of billions of dollars in volume, led zero-to-one bets, and scaled Stripe Atlas so that one in six new Delaware corporations are started on it, known for his go-go-go-plus-optimistic long-term compounding approach, Stripe Study Groups for practicing customer empathy, and being deeply responsive to customer feedback on Twitter.

The Operator The Craftsperson

Dimension Profile

Strategic Vision 60%

Execution & Craft 90%

Data & Experimentation 60%

Growth & Distribution 40%

Team & Leadership 55%

User Empathy & Research 90%

Key Themes

go-go-go optimism plus long-term compounding Stripe Study Groups for customer empathy measuring value from the customer's perspective breaking walls between PMs and customers product craft and quality obsession scaling payment infrastructure globally

Episode Summary

Jeff Weinstein provides an archeology of effective product leadership at Stripe, centered on his philosophy of pairing go-go-go optimism with long-term compounding investment. He shares the Stripe Study Groups program where teams practice customer empathy by pretending to be companies with problems (with the rule that they're not there to solve anything), explains why he'll leave a meeting to respond to a customer complaint on Twitter, and tells the story of how Stripe went from 10 to 100+ payment methods by investing in infrastructure over immediate wins.

Leadership Principles

→ The moment the customer felt compelled enough to go out of their way to talk about some problem, that's an unbelievable gift — leave a meeting to get one message back to them
→ Go, go, go ASAP plus optimism paired with long-term compounding — inject energy to move fast today while investing in things you'll never regret spending time on
→ Study Groups: four to eight people pretend to be some company with some problem, rule one is you do not work at Stripe, rule two is we're not here to solve any problems, just practice empathy

Notable Quotes

"The moment the customer felt compelled enough to go out of their way to talk about some problem, that's an unbelievable gift. I will leave a meeting to just get one message back to them."
— On treating customer feedback as a precious signal

"We show up, four to eight people total, pretend to be some company with some outcome problem. Rule one is you do not work at Stripe and rule two is we're not here to solve any problems. This is just about practicing empathy for the customer."
— On the Stripe Study Groups program he created

"We'll never regret spending time making the latency of our payments APIs faster. We'll never regret making it more reliable to send 83B election mails to the IRS. Let's just always compound those capabilities over time."
— On identifying investments that always compound

Want to know how you compare?

Take the Assessment