Field notes on building
technology businesses.
Engineering leadership, DORA metrics, and AI-native transformation, written from 25 years at the seam between the boardroom and the codebase.
From Low Performer to Elite: A Three-Month DORA Transformation
How a struggling engineering organization went from fearful, manual releases to elite DORA performance in ninety days, and why process, not heroics, did the work.
Read the essay →Agile Is Dead. The Word Is Still Twitching.
Agile was a workaround for the slow, expensive nature of building software in 2001. AI repriced the building. The ceremonies that compensated for the old expense are now a tax paid in the exact currency they were invented to protect: speed.
Read →Your Company Doesn't Adopt AI. AI Digests Your Company.
AI is the first technology that metabolizes organizations rather than augmenting them. Going "AI-native" doesn't upgrade your operating model — it dissolves the structure that existed to manage problems AI just erased.
Read →Product Management Was a Workaround. AI Removed the Thing It Worked Around.
Product management was an optimization layer for a constraint—expensive software—that no longer exists. When building gets cheap, the PM's job inverts: from advocate for what gets built to editor of what shouldn't.
Read →Automating Your Support Queue Is the Worst Use of AI Your Company Will Make This Year
A support ticket isn't a cost to be deflected. It's the highest-fidelity evidence you have about where your product, pricing, and onboarding are broken — and the standard AI playbook is quietly destroying it.
Read →AI Coding Ate the Staff Engineer First. Nobody Wants to Talk About It.
Everyone expected AI coding to come for junior engineers. The role it's quietly absorbing is staff engineer—and the new scarce resource isn't generating code, it's verifying it.
Read →Business Before Backlog
Most roadmaps are a pile of features looking for a reason. The fix is to start from the product and the P&L, then build the engineering to match.
Read →Read the Thesis Before the Code
Architecture is a means, not an end. Before I judge a system, I learn what the business is trying to become.
Read →Becoming AI-Native: Rebuilding the Operating Model, Not Just the Product
Most companies are bolting AI onto an operating model designed for a pre-AI world. Going AI-native means rewiring how products are built and how the organization runs.
Read →The Kind of CTO You Need at Each Stage
The CTO who takes you from zero to one is rarely the one who scales you to a hundred. A field guide to matching the leader to the moment.
Read →Measuring Engineer Productivity Without Breaking Trust
Productivity metrics turn toxic the moment they're used to rank people. Here's how to measure the system instead of the individual, and still get the leverage leadership wants.
Read →The Unhealthy Fixation: Why I Obsess Over Operator Experience
Everyone talks about user experience. The experience that quietly decides whether a software business scales is the one nobody designs for, the operator's.
Read →On-Prem to Cloud-Native With Under an Hour of Downtime
Big-bang migrations fail loudly. Here's the incremental, reversible approach I use to move legacy systems to the cloud while the business keeps running.
Read →