Datadog Deleted All Its AI Context. It Worked.

Datadog's Language Foundations team deleted an entire folder of AI context files that had been carefully written and maintained for over a year, expecting a performance hit. Instead, their evals got better. Simon Boudrias, who runs Language Foundations at Datadog, walks Guy through what that taught his team about context rot, and the full journey of scaling AI coding agents to 4,000 engineers. What we cover: – How Datadog scaled Cursor and Claude Code to 4,000 engineers in under a year – Why...