About Jesse Robbins | Early Stage Investor, Founder, Builder

Jesse Robbins is a founder, investor, and firefighter whose career sits at the intersection of high‑growth startups, critical infrastructure, and real‑world emergency response. He is perhaps best known for pioneering modern cloud infrastructure automation and starting the DevOps movement.

As an investor, Jesse focuses on developer tools, cloud infrastructure, and increasingly AI/ML and intelligent systems. He is currently General Partner at Heavybit, a developer‑focused venture firm, where he sources and leads investments and works with founders on go‑to‑market, product, and company‑building. He has been deeply involved as an investor, advisor, and board member with Heavybit’s most successful portfolio companies including Sanity, LaunchDarkly, PagerDuty, Blockdaemon, CircleCI, and Tailscale.

Jesse’s operating career is anchored in his work as the founding CEO of Chef (formerly Opscode), an early pioneer of cloud infrastructure automation. Under his leadership, Chef became a widely adopted platform used by thousands of organizations around the world and by companies such as Facebook, Google, Apple, and IBM, and was ultimately acquired by Progress Software. He later founded Orion Labs, a real‑time AI voice platform for frontline and “heads‑up” teams, where he served as CEO and then Executive Chairman and board member.

Before Chef, Jesse served as Amazon’s “Master of Disaster,” responsible for the availability of every property bearing the Amazon brand. There he created Amazon’s Incident Management and GameDay programs—structured, high‑stakes drills that purposely induced major system failures to train teams and improve reliability—and founded O’Reilly’s Velocity Web Performance and Operations Conference to help spread these practices. In recognition of his work with Amazon, Chef, and Devops movement, he was recieved an MIT TR35 award for top innovators under 35.

A constant through all of this is Jesse’s background in emergency services. After an early startup role that led to an IPO in the late 1990s, he stepped away from tech to complete Firefighter/EMT training and went on to serve as a volunteer Firefighter/EMT and Emergency Manager, including leading task forces deployed during Hurricane Katrina. That experience, combined with decades of startup building and investing, informs his views on leadership, resilience, and how teams perform under pressure.