Navigating the Tech Evolution in Product Development

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.

In this episode, you’ll learn:

1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI

2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills

3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers

4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence

5. How “vibe coding” is changing how companies operate

6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)

7. “Model maximalism” and why today’s AI is the worst you’ll ever use again

8. Practical prompting techniques that improve AI interactions, including example-based prompting

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Where to find Kevin Weil:

• X: https://x.com/kevinweil

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

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Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

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In this episode, we cover:

(00:00) Kevin’s background

(04:06) OpenAI’s new image model

(06:52) The role of chief product officer at OpenAI

(10:18) His recruitment story and joining OpenAI

(17:20) The importance of evals in AI

(24:59) Shipping quickly and consistently

(28:34) Product reviews and iterative deployment

(39:35) Chat as an interface for AI

(43:59) Collaboration between researchers and product teams

(46:41) Hiring product managers at OpenAI

(48:45) Embracing ambiguity in product management

(51:41) The role of AI in product teams

(53:21) Vibe coding and AI prototyping

(55:55) The future of product teams and fine-tuned models

(01:04:36) AI in education

(01:06:42) Optimism and concerns about AI’s future

(01:16:37) Reflections on the Libra project

(01:20:37) Lightning round and final thoughts

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Referenced:

• OpenAI: https://openai.com/

• The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/

• Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/

• Waymo: https://waymo.com/

• X: https://x.com

• Facebook: https://www.facebook.com/

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

• Planet: https://www.planet.com/

• Sam Altman on X: https://x.com/sama

• A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k

• OpenAI evals: https://github.com/openai/evals

• Deep Research: https://openai.com/index/introducing-deep-research/

• Ev Williams on X: https://x.com/ev

• OpenAI API: https://platform.openai.com/docs/overview

• Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720

• Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons

• StackBlitz: https://stackblitz.com/

• Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet

• Anthropic: https://www.anthropic.com/

• Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile

• Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i

• Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/

• Figma: https://www.figma.com/

• Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/

• Andrej Karpathy on X: https://x.com/karpathy

• Silicon Valley CEO says ‘vibe coding’ lets 10 engineers do the work of 100—here’s how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/

• Cursor: https://www.cursor.com/

• Windsurf: https://codeium.com/windsurf

• GitHub Copilot: https://github.com/features/copilot

• Patrick Srail on X: https://x.com/patricksrail

• Khan Academy: https://www.khanacademy.org/

• CK-12 Education: https://www.ck12.org/

• Sora: https://openai.com/sora/

• Sam Altman’s post on X about creative writing: https://x.com/sama/status/1899535387435086115

• Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency)

• Novi: https://about.fb.com/news/2020/05/welcome-to-novi/

• David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/

• Peter Zeihan on X: https://x.com/PeterZeihan

• The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R

• Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G

• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske

• MySQL: https://www.mysql.com/

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Recommended books:

• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X

• The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341

• Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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