The Devops Engineer Who Never Sleeps — Diamond Bishop, Datadog
Apr 22, 2025 · 16:18
Diamond Bishop, Director of AI Engineering at Datadog, explains how his team builds AI agents—the On-Call Engineer and Software Engineer—that automate DevOps tasks like incident investigation, remediation, and postmortem writing. He details how the On-Call Engineer wakes up for alerts, reads runbooks, queries logs and metrics, and suggests fixes to let human engineers sleep. The Software Engineer proactively fixes errors by generating code diffs and pull requests. Bishop shares four key lessons: scope tasks and evaluate rigorously, assemble teams of optimistic generalists and UX experts, adapt UX for human-agent collaboration, and treat observability as critical for debugging multi-step agent workflows. He predicts that within five years, AI agents will surpass humans as primary users of SaaS platforms like Datadog, urging builders to design for agent consumers.
