About Jesse Robbins | Early Stage Investor, Founder, Builder

Jesse Robbins is a founder, investor, and firefighter whose career sits at the intersection of startups, infrastructure, and real-world emergency management. He is perhaps best known for starting the DevOps movement, pioneering cloud infrastructure automation as founder & CEO of Chef, and for being an early investor and advisor in startups like Fastly, Instacart, PagerDuty, Sanity, CircleCI, LaunchDarkly, Blockdaemon, and Tailscale.

As an investor, Jesse focuses on developer tools, cloud infrastructure, and AI. He is currently a 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, or board member—with some of Heavybit’s most successful portfolio companies, including Sanity, LaunchDarkly, PagerDuty, Blockdaemon, CircleCI, and Tailscale.

Jesse was founding CEO of Chef the early pioneer of cloud infrastructure automation. Under his leadership, Chef became a widely adopted platform used by thousands of organizations around the world, including 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.

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 deliberately 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 at Amazon, Chef, and in the emerging DevOps community, he received MIT Technology Review’s 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 a task force deployed during Hurricane Katrina. That experience, combined with decades of startup building and investing, informs his views on leadership, resilience, and how teams can succeed under pressure.