Engineering Leadership

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The Non-Product Surface Area

Every time I’ve watched a company get built from the inside, the same thing happens. The founders pick a product direction, start shipping, and for a few quarters…

The Org Chart Is Flattening & Nobody Has a Replacement

Two things happened last week that look unrelated but aren’t. JPMorgan told its 65,000 engineers and technologists that AI tool usage is now part of their performance reviews.…

“Tokenmaxxing” Is Lines-of-Code Thinking for the Agentic Era

Silicon Valley has a new competitive sport, and it’s exactly the mistake you think it is. The New York Times reported last week that engineers at Meta, OpenAI,…

Your AI Notetaker Is the Biggest Security Decision You’re Not Making

Every engineering leader I know is running at least one AI meeting recorder. Fathom, Otter, Fireflies, Granola — they show up in your Zoom call, they transcribe everything,…

Minutes Added To Workforce

Every company I’ve talked to in the last two quarters is asking the same question about AI: what’s the ROI? The instinct is to measure AI value in cost…

Block Just Cut 3,500 Jobs. You’re Reading It Wrong.

Jack Dorsey announced this week that Block is cutting roughly 3,500 people — about 40% of its workforce. The stock has been sliding for years. The headlines are…

Are You Managing Your Manager? (The Agentic Update)

In 2015, I stood in front of a room full of engineers at Code Driven NYC and laid out a formula for how individual contributors could take charge…

Can AI Solve the Four Burner Problem?

In my last post, Awe in an AI World, I wrote about the reclaimed time that AI is creating and the question that keeps me up at night in…

The Next Platform Giant Is Hiding in Plain Sight

Every major era of software development has produced a defining platform company. The one that quietly became the infrastructure everyone depends on. GitHub didn’t win because git was…

Awe in an AI World

I’ve spent most of my life implementing systems at scale, watching engineering teams transform how they work (pre- and post-AI), and having thousands of conversations about what it…

The notebook, in your inbox.

The notebook, in your inbox. Every Tuesday, one essay on AI implementation, engineering leadership, or the operator-to-founder transition. No digests, no roundups, no AI-generated news — just the ideas I'm actually working through.