Dylan Vassallo is an engineering manager at OpenAI leading the People Innovation Labs team — an eng, product, and design team embedded within the People org, building AI-powered tools for recruiting, HR, internal comms, and the employee experience.

In this episode, Dylan talks about what it actually looks like to be an engineering team inside a frontier AI company, how non-engineers are becoming builders, and what the "graduation" process looks like when a prototype needs to become a production system.

Links & References

https://x.com/dylanvee
OpenAI Codex - https://openai.com/codex
Lattice - https://lattice.com — performance management platform mentioned
Linear - https://linear.app — used for team project tracking
Workday - https://workday.com — referenced as system of record

Hosts: Alex Kessinger & David Noël-Ramos

Guest: Karynn Ikeda — Former Engineering Manager → AI Enablement Program Manager at Babylist @ktikeda

Karynn Ikeda shares the full arc of how Babylist adopted AI across its engineering organization — from a six-week Windsurf pilot on a single team, to company-wide Claude Code adoption and a bold initiative to onboard product managers and designers into the codebase. She discusses leadership buy-in, measuring developer sentiment over raw velocity metrics, the shift toward agent orchestration, and why the return of joy and creative empowerment may be the most important signal of all.

Links & References

• Karynn Ikeda (@ktikeda)
• Babylist babylist.com
• Shopify CEO Tobi Lütke's AI Memo (April 2025) Original post on X
• Anthropic Code Review for Claude Code claude.com/blog/code-review
• Claude Code code.claude.com
• Devin (AI coding agent by Cognition) devin.ai
• Cursor cursor.com
• Windsurf windsurf.com
• Lovable (vibe coding tool) lovable.dev
• V0 (by Vercel) v0.dev

Will Maier leads growth engineering at Stripe, where he's spent the last five years working across nearly every surface of the product. His background isn't CS — it's the history of science — and he's been through enough industry shifts (racking servers, the cloud transition, DevOps) to know when something really big is happening.

Find us now also on YouTube: @StaffEngPodcoast

In this season premiere of StaffEng, Will joins Alex and David to talk about what changed for him after November 2025, why he spent the holidays building a Lua distribution from his phone while doing laundry, and how he thinks about the organizational dynamics of AI adoption inside a large engineering org.

Topics covered:

• Why Will hasn't opened an IDE since November — and what replaced it
• The psychology of AI adoption: shame, hallucinated PRs, and "AI vegans"
• Skills as the new packages: how improvised markdown files are changing how teams share leverage
• Why measuring token usage (the wrong metric) surfaced the right insights
• The case for making the incident report critic, not the incident report writer
• What the cloud and DevOps transitions teach us about where AI is headed