Jason Derr

Writing

Thoughts on AI product management, development, and leadership.

SecurityDecember 11, 202516 min read

A Vibe Coder's Guide to Not Shipping Vulnerabilities

New research shows 83% of AI-generated code that passes tests contains exploitable vulnerabilities. Here's what the data reveals and what actually works to ship secure code.

AgentOpsJuly 26, 20259 min read

Why AI Observability Beats AI Performance

While everyone obsesses over the latest AI models and context windows, the companies actually scaling AI are solving a much less glamorous problem. They can see what their agents are doing.

AI StrategyJune 15, 202511 min read

Why Your AI Strategy Needs a Reality Check

Most enterprise AI projects fail not because the technology is inadequate, but because consultants are selling deterministic promises for probabilistic systems.

TechnicalMay 8, 202512 min read

Evolving AI Evaluation: What I Learned Building Creative Content Systems

How implementing evaluation methodology at Templatiz revealed new evaluation paradigms for creative AI systems.

AI StrategyApril 1, 20255 min read

Most Teams Aren't Failing—They're Succeeding at the Wrong Thing

Why product models break, and how to lead with impact. A look at the 'low-impact death spiral' and how to realign teams around business-critical outcomes.

AI StrategyMarch 20, 20258 min read

Why AI Products Break Traditional Value Propositions

Most AI products fail not because their technology is inadequate, but because they're using 20th-century value proposition frameworks for 21st-century technology.

StrategyJanuary 2, 202512 min read

I Turned Down an AI PM Job Because I Couldn't See a Moat

I got to the final round of an AI PM interview. The company was early-stage, experienced team, solid funding, growing fast. They wanted to move forward. I said no.