“I’ve done migrations similar to this before we had these kind of tools and it was a very different world.”

In this episode of Datadog Illuminated, Nick Isaacs, engineer on Datadog’s AI DevX team, walks through the LLM-powered workflow his team built to migrate thousands of HTTP endpoints out of Datadog’s webapp monolith into microservices.

The system pairs Claude Code for transformation with GPT-5 for code review, orchestrated by LangGraph, with a self-correcting verification loop that runs the type checker, tests, and server start and fixes its own errors before a human sees the PR.

Watch here: youtu.be/6KlZVvLSM…

Whitney Lee (left, smiling broadly, curly red hair) and Nick Isaacs (right, wearing headphones) flank a lightboard covered in a handwritten workflow diagram. Large neon-style text reads "Using AI to Dismantle Our Monolith." The Datadog Illuminated logo appears in the top left corner, and Nick's name is displayed in the bottom right. The background is a dark brick wall with colorful neon light accents.