Reflections on Tenure and the Pursuit of Continuous Learning

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.

Episode Links:

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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

(00:37:43) How to communicate well

(00:46:14) How managers can scale themselves

(00:51:17) How to build a new engineering site

(01:01:21) What kept him at Google

(01:03:57) The story behind joining Stripe

(01:12:34) Comparing and contrasting cultures

(01:20:55) How to set culture

(01:29:25) Is Stripe too reliable?

(01:33:48) Hiring at scale without Leetcode

(01:38:06) Lessons learned working with Stripe's leadership

(01:40:31) Why leave Stripe

(01:44:55) How his AI startup plans to compete

(01:48:46) Career reflections, regrets, what went well

(01:54:03) Top book and habit that impacted his career

(01:57:40) Advice for younger self

(01:59:04) Outro

Where to find David:

• If you are a builder: https://sdsa.ai/build

• If you are very excited about what they are building and would consider joining his talent dense team, you can email David here: dps@sdsa.ai

• X/Twitter: https://x.com/dps

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

• Threads: https://www.threads.com/@davidsingleton

Where to find Ryan:

• Newsletter: https://www.developing.dev/

• X/Twitter: https://x.com/ryanlpeterman

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

• Threads: https://www.threads.com/@ryanlpeterman

• Instagram: https://www.instagram.com/ryanlpeterman

• TikTok: https://www.tiktok.com/@petermanpod

This episode was produced with the help of SF Podcast Studio: https://www.sfpodcast.studio/