Lenny's Podcast: Product | Career | Growth

AI’s third era: the rise of persistent AI coworkers | Tara Seshan (OpenAI’s product lead)

August 30, 2026

AI Summary

5 min read

"Before enlightenment, chop wood, carry water. After enlightenment, chop wood, carry water." For Tara Seshan, OpenAI’s product lead for ChatGPT and Codex, that Zen saying captures how the team behind Codex succeeded: the internal operating mode never changed, even as the outside world suddenly noticed. The team was always obsessed with users, always dogfooding, always iterating. The market just caught up.

Seshan joined OpenAI a year ago, and she describes the shift from her previous roles at Stripe and Watershed as a move from a theoretical, academic approach to a deeply empirical one. In a market that is “very emergent, very fast changing,” writing a long strategy document is less valuable than forming a sharp hypothesis and testing it with users as fast as possible. The core of product management, she argues, has not changed—it is still about asking the most essential question, testing it, and feeding results back into the loop. But now, that core is the only thing that matters. The trappings of the role have fallen away.

The shift from theoretical to empirical

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What you'll learn

1 (00:00) **Three Eras of AI Products** - Tara introduces a framework: chat era, agent era, and the coming persistent co-worker era
2 (02:22) **What Surprised Tara About Working at OpenAI** - The company is founder-led and surprisingly transparent, with no secret playbook
3 (06:48) **Why Empirical Trumps Theoretical at AI Speed** - In slow markets you can do grand strategy; in AI you must test fast
4 (09:04) **The Core of PM That Hasn't Changed** - Problem definition and testing loop is more essential than ever
5 (11:22) **The Future of Work: Steering vs. Rowing** - Knowledge workers will shift from doing to directing agents
6 (16:55) **From One-on-One Agents to Multi-Agent Collaboration** - The next frontier is agents that work together as teammates
7 (19:08) **The Tactical Challenges of Making Agents Useful** - Intelligence alone isn't enough; infrastructure and data access matter hugely

+ Full timestamped outline available in the app

Show Notes

Tara Seshan leads product for Codex and ChatGPT Work at OpenAI (alongside previous podcast guest Andrew Ambrosino, who’s her engineering manager). Before OpenAI, Tara spent over six years at Stripe, where she joined as one of the first five product managers. She went on to lead product for Watershed, which Time magazine named one of the best inventions of 2022, and she is also a founder and Thiel Fellow. Most personally meaningful to me: Tara is one of the three inaugural Lenny’s Newsletter Fellows, a program I ran a couple of years ago to spotlight the most exciting up-and-coming product leaders.

In our in-depth conversation, we discuss:

1. The shift from “rowing” to “steering,” and why human judgment and ambition will become differentiators as AI takes on execution

2. How OpenAI thinks about building for model capabilities two to three months out

3. OpenAI’s best internal memes, such as “Is this maximally accelerated?” and “Are you mainlining it yet?”

4. Why ambition is the new bottleneck for companies, and why elevating others’ ambitions is now the key part of the PM job

5. Writing as thinking vs. writing as reporting

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Where to find Tara Seshan: