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

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

August 30, 2026 • 1 hr 21 min
🎧 Listen Now

🤖 AI Summary

Overview

This episode explores the evolving role of AI in knowledge work, focusing on the shift from execution (rowing) to strategic guidance (steering). Tara Seshan, OpenAI's product lead for Codex and ChatGPT Work, shares insights into OpenAI's culture, the future of AI as a persistent coworker, and how product management is adapting to the rapid evolution of AI capabilities. The conversation also delves into the importance of ambition, the changing nature of work, and the role of human creativity in an AI-driven world.


Notable Quotes

- You fail if you build for where the models are now, and you fail if you build for where you think the models will be in a year. Both outcomes are equally wrong. The only way to build is two to three months ahead. — Tara Seshan, on the challenges of building AI products in a fast-evolving landscape.

- The future of work will look more like steering than rowing. There will be agents that do the rowing, and your role increasingly becomes steering the ship in the right direction. — Tara Seshan, on the changing nature of knowledge work.

- The hardest part is expanding your thinking. The capabilities have expanded so dramatically, but your ambitions are no longer limited by what you're capable of executing yourself. — Tara Seshan, on the transformative potential of AI tools.


🚀 The Evolution of AI in Knowledge Work

- Tara Seshan describes the progression of AI from chat-based tools to agents, and now to persistent AI coworkers that can collaborate with humans.

- The future of work will involve humans steering while AI agents handle the rowing — executing tasks and providing insights.

- OpenAI envisions agents as persistent teammates that can work independently, take feedback, and collaborate with humans and other agents.

🧠 The Changing Role of Product Managers in the AI Era

- PMs must shift from theoretical, long-term planning to rapid, empirical experimentation.

- Tara emphasizes the importance of defining sharp hypotheses and testing them quickly with users.

- The core of the PM role remains identifying the most critical questions about a product and iterating based on user feedback.

🔥 Ambition as the New Differentiator

- With AI making routine tasks easier, Tara argues that ambition is now the key differentiator for individuals and companies.

- PMs play a crucial role in elevating their teams' ambitions, challenging them to think bigger and move faster.

- OpenAI's internal culture emphasizes this with memes like Is this maximally accelerated? and Are you mainlining it yet?

🛠️ Building for the Future of AI Models

- OpenAI's product strategy focuses on building for where AI models will be in two to three months, not where they are now or where they might be in a year.

- This requires close collaboration between product teams and researchers to anticipate and align with upcoming model capabilities.

- The rapid iteration cycle at OpenAI is driven by a culture of dogfooding, user feedback, and a willingness to ship imperfect products to learn quickly.

🎨 Human Creativity and AI Collaboration

- Despite AI's growing capabilities, Tara highlights the enduring importance of human judgment, creativity, and accountability.

- She likens software development to filmmaking, emphasizing the role of human intuition and artistry in creating compelling products.

- OpenAI is working to make AI a better collaborator in knowledge work by focusing on transparency, reasoning, and process visibility.

AI-generated content may not be accurate or complete and should not be relied upon as a sole source of truth.

📋 Episode Description

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

—

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

—

Where to find Tara Seshan:

• X: https://x.com/tarstarr

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

• Newsletter: https://substack.com/@taraseshan

—

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

—

In this episode, we cover:

(00:00) Introduction

(02:18) What makes OpenAI’s culture so different

(06:42) Why AI product strategy is all about fast experimentation

(09:02) How the PM role is changing

(10:50) The shift from rowing to steering

(15:35) What changes when agents become coworkers

(20:05) Why ambition matters more than ever

(26:39) Building products for models that do not exist yet

(29:21) How ChatGPT’s Chat and Work modes differ

(34:01) How OpenAI ships so quickly