OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter)

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: htt