Ex-Stripe CTO on What Grew His Career, Hiring Without Leetcode, Coding as a Leader (Career Story)

The Peterman Pod

Aug 29, 2025•2 hr

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Summary

David Singleton, a seasoned engineering leader from Google and Stripe, delves into critical aspects of career growth, emphasizing continuous learning and the pivot from individual contributor to management. He shares unique insights on scaling engineering organizations, including the "engineer-cation" concept for senior leaders, effective communication strategies, and building remote sites. The episode also covers Stripe's approach to achieving high reliability and its non-Leetcode hiring process, culminating in Singleton's new venture, DevAgents, and his reflections on leadership and company culture.

Episode description

David Singleton was the CTO at Stripe for 7 years before he left to start /dev/agents. Prior to Stripe, he grew from a junior engineer to a VP at Google. I recently asked him about everything he knows about career growth and being an excellent engineering leader. We discussed how Stripe hired at scale without Leetcode, why he thinks all engineering leaders should write code, the book that impacted his career most and many more topics.

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Timestamps:

(00:00:00) Intro

(00:00:56) Before Google

(00:06:34) Joining Google

(00:12:56) Deciding to try management

(00:24:15) How to decide on EM vs IC

(00:28:58) Biggest gap in managing managers

(00:34:21) The difference between VP and Senior EM