Overcoming the Fear of Making Your First PR

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What does “AI-native” actually look like inside a company — not in theory, but in practice?In this episode of Supra Insider, Marc and Ben sit down with James Dillard, former YouTube and Stripe PM, who recently spent three months embedded at Roo Code, an AI-native startup building coding agents that can write and review production code.

James shares what it was like to join a 10-person team where everyone contributes to the codebase — from designers to community managers — and where the product process has been reimagined from the ground up.He walks through how discovery, design, and iteration actually work in an environment where code is the default language of collaboration — and what that means for the future of product management, engineering, and org design.

Whether you’re a product leader trying to make your org more AI-native, a founder exploring new operating models, or just curious about what “AI-native” means beyond the buzzwords — this episode offers a rare inside look at how the next generation of teams are really working.

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Interviewing at Uber, Figma, Stripe, or DoorDash?

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In this episode, we covered the following topics:

* (02:12) What makes Roo Code different—minimal permission-seeking agents and rethinking team structure

* (04:34) How and why every team member ships code (even support and marketing)

* (08:33) Facing the fear of shipping your first PR as a non-engineer

* (12:30) How AI is breaking traditional GitHub PR flows with cheaper, more frequent pull requests

* (15:50) What a product development cycle looks like in an AI-native team

* (26:03) Design systems as strategic leverage—and who gets to shape them

* (35:59) Why defining the type of feedback matters more than ever

* (48:30) Guardrails and the need for new review patterns to handle contributor sprawl

* (52:27) Can non-AI-native companies adopt this way of working—or must they start from scratch? The 4-part framework.

* (58:55) Rethinking core PM values like “sell before you build” in a world where you can ship a prototype in minutes

* And more!

Links:

* James’s email: hello@jdilla.xyz

* James’s blog: https://www.jdilla.xyz/blog

* James’s YouTube Channel: https://www.youtube.com/@dangerously-skip-permissions

* James Dillard: https://www.linkedin.com/in/jamesdillard/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

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