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Writing · Tag
8 posts on engineering leadership. Or browse the full writing index →
Replit's AI agent ignored a code freeze, wiped a production database in nine seconds, then confessed it violated every principle it was given. The strongest case yet for hiring MORE senior engineers in the AI boom — not fewer.
Every company rolling out AI is about to discover how much work they were leaving on the table. AI doesn't replace headcount — it surfaces the backlog you never had bandwidth to touch. The math behind why velocity creates surface area, the failure mode that follows, and why the companies cutting headcount now are about to get outpaced.
Most engineers using Claude Code see a 10–15% speedup. The teams seeing 40–55% aren't typing faster — they're sequencing work differently. The four modes I use AI in, what to never delegate, and how to get a skeptical team across the line.
The title 'Staff Engineer' means three different things at three different companies. At an AI startup pre-Series-A, only one of those three is what you actually need. The screen, the take-home, the interview loop, and the AI-fluency calibration that's now table stakes.
I went from sole engineer to running a 15-person engineering organization over four years at a startup I co-founded. The hardest lessons weren't about code. The six things I'd tell my younger self.
Most pre-Series-A AI founders hire in panic order, not strategic order. The result is a team that can't ship the product the company actually needs. The hire-by-hire plan I'd run, who comes first, and why hire #4 isn't another engineer.
A fractional engineering engagement starts with a codebase you've never seen. You have ninety minutes to form a useful POV before the kickoff call. The seven-step triage I run, the two questions I bring back to the founder, and how AI tooling has accelerated the process.
A 4-person engineering team is the most overlooked unit of management in startups. Big enough that the lead can't write all the code. Small enough that hiring an EM kills velocity. Five rituals that work at this size, three traps to avoid, and the signal that tells you it's time to evolve.