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Ex-Stripe CTO on What Grew His Career, Hiring Without Leetcode, Coding as a Leader (Career Story)
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:• Transcript• Youtube• AppleTimestamps:(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) OutroWhere 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: [email protected]• X/Twitter: https://x.com/dps• LinkedIn: https://www.linkedin.com/in/davidpsingleton/• Threads: https://www.threads.com/@davidsingletonWhere 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/@petermanpodThis episode was produced with the help of SF Podcast Studio: https://www.sfpodcast.studio/
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1:59:39
Behind the Scenes of this Podcast So Far (25,000 Sub Special)
We hit 25,000 subscribers! 🎉🎉🎉Thanks so much to everyone who has supported my work, never thought we'd be here let alone this fastHad some spare studio time booked and figured I might as well use it as time for an FAQ episode. This episode is for anyone whose curious about some of the story behind the podcastFeeling very lucky, thank you all! 🙏Also if you have any feedback for me about the show and how to make it better, I'd love to hear it. Feel free to drop a commentTimestamps:(00:00) Intro(00:58) Story behind the podcast(05:30) Behind the scenes of the top episodes(10:06) Dream guest list (12:03) Learnings from podcasting (13:10) Balancing content with a full time job (14:28) Outro
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Meta Senior Manager (M2) on Manager Career Growth, PIPs, Amazon vs Meta | Stefan Mai
Stefan Mai was a Senior Manager (M2) with experience across Meta and Amazon. We went over his career story in growing to M2 which is equivalent to Senior Staff (IC7) in big tech. Since he started his own company now, he was happy to be fully transparent about the behind the scenes of managing in big tech. Since he founded the interview prep company, Hello Interview, I also thought it’d be interesting to talk about trends he’s seeing in AI cheating tools and how to get offers at OpenAI/Anthropic. We discussed:• Meta Senior Manager (M2) career growth story• Amazon vs Meta culture• Which company had stronger engineers• How low performer quotas & PIPs work• Eng vs manager career growth• Transitioning to AI/ML as an eng• Getting offers at OpenAI and Anthropic• Advice for his younger selfTimestamps:(00:00) Intro(00:59) Early career at Amazon (05:46) Growth to eng manager at Amazon(11:31) Storytelling tips(16:28) Why he left Amazon(22:59) Transitioning to AI/ML(27:01) Senior manager (M2) promo story at Meta(31:30) Mutiny and manager politics(40:34) Are managers harder to layoff?(49:50) Senior manager (M2) skill gaps(53:21) Eng vs manager career growth(56:27) Amazon vs Meta culture(01:00:34) Amazon vs Meta performance(01:05:24) Low performer quotas(01:08:55) Can you get out of a PIP?(01:12:23) AI interview cheating(01:16:42) Passing OpenAI & Anthropic interviews(01:18:33) Job hopping(01:22:37) When he grew the most(01:24:22) How to write better (01:26:22) Career motivations past M2(01:28:11) Advice for younger selfWhere to find Stefan:• LinkedIn: https://www.linkedin.com/in/stefanmai/• His company: https://www.hellointerview.com/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
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1:31:26
Instagram Staff (IC6) Promo Despite 10 Team Switches in 9 Years (Career Story)
Sash Zats grew to be a Staff Engineer (IC6) at IG despite switching teams 10 times in 9 years. His career journey was a series of jumps to exciting projects and letting career growth happen as a byproduct. I interviewed him to show you how team switches can play out. We discussed:• How 10 team switches in 9 years affected his career• The story behind the Instagram blockchain initiative• His 2 diff in 6 month performance review• What working on Instagram Threads was like pre-launch• The value of prototypingTimestamps:(00:00) Intro(00:49) First team: iOS on Newsfeed Delight(05:30) What makes a good designer partner? (08:30) Joining a hardware team (12:08) 2 diffs in 6 months (15:03) Joining the Instagram blockchain team(21:37) Joining Instagram Threads pre-launch (28:53) Working with an exceptional engineer (Peter)(33:02) Working on AI prototyping teams(37:15) Reflecting on team switching’s impact on career growth (44:35) Why leave Meta (46:15) Advice for younger self (47:53) Outro Where to find Sash:• LinkedIn: https://www.linkedin.com/in/sashzats/• X/Twitter: https://x.com/zatsWhere 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
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Amazon VP On Promotions, Getting Fired Twice, Working With Bezos | Ethan Evans
Ethan Evans went from being fired twice because of poor soft skills to getting promoted to Vice President at Amazon with a team of over 800 engineers. I asked him about everything he learned along the way.We discussed:• Being fired for poor soft skills• What VP promotions look like• Working with Jeff Bezos and Andy Jassy (current Amazon CEO)• VP performance reviews• Stack ranking, PIPs and how managers can fire anyone• Advice for his younger selfTimestamps:(00:00) Intro(01:01) Experience before Amazon(05:03) Getting fired twice & learnings(14:02) Joining Amazon(16:02) What VP promotions look like(26:03) Promotion failure story(29:14) Integrating Twitch into Amazon(33:48) Jeff Bezos vs Andy Jassy stories(36:53) VP performance reviews (41:10) Stack ranking & PIPs(46:11) A manager can fire anyone they want(50:45) Advice for his younger self(53:03) OutroWhere to find Ethan:• LinkedIn: https://www.linkedin.com/in/ethanevansvp/• X/Twitter: https://x.com/EthanEvansVP• Newsletter: https://levelupwithethanevans.substack.com/• YouTube: https://www.youtube.com/channel/UC-BAdkBGjOIlccGLZ3jbLiAWhere to find Ryan:• 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• Newsletter: https://www.developing.dev/
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53:25