Jonathan Wondrusch (Block): Raising Ambition in the Singularity Artwork

StaffEng

Conversations with software engineers who have progressed beyond the career level, into Staff levels and beyond. We discuss the areas of work that set Staff-plus level engineers apart from other individual contributors; things like setting technical direction, mentorship and sponsorship, providing engineering perspective to the org, etc.Hosted by David Noël-Romas (@davidnoelromas) and Alex Kessinger (@voidfiles).

All Episodes

StaffEng

Jonathan Wondrusch (Block): Raising Ambition in the Singularity

July 26, 2026 • David Noël-Romas (@davidnoelromas) and Alex Kessinger (@voidfiles) • Season 2 • Episode 5

0:00 | 51:24

Jonathan joins Alex and David to talk about what actually changes when agents get good enough to do the work. He walks through the 60-service monorepo migration that convinced him the ceiling had moved, why "raising ambition" is now a real coaching conversation with his team, and how Block is using linters and LLM-as-judge to keep GraphQL API design honest.

The conversation goes past the usual velocity story into the harder question: engineering is multiplayer, and most AI tooling is still single-player. Jonathan makes the case that the human touch points — design reviews, pairing, cross-functional feedback — are the part you have to deliberately protect, not the part you optimize away. Plus: adversarial code review with mixed models, why he'll let an agent write his code but not his voice, and the trap of low-hanging fruit that doesn't compound.

https://x.com/JWondrusch

https://x.com/davidnoelromas

https://x.com/voidfiles