About — Founder, Builder, Investor
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.
Frequently Asked Questions
What is Jesse Robbins known for?
Jesse Robbins is known for starting the DevOps movement, founding Chef Software (the infrastructure automation platform acquired by Progress Software), and pioneering chaos engineering practices at Amazon. He also founded Orion Labs, a real-time AI voice platform, and the O’Reilly Velocity Conference. He is currently an early-stage investor focused on developer tools, cloud infrastructure, and AI.
How did Jesse Robbins start the DevOps movement?
Jesse Robbins co-founded the O’Reilly Velocity Web Performance and Operations Conference, which became the gathering point for practitioners who were bridging software development and IT operations. Drawing on his experience managing availability at Amazon scale, he helped codify the practices and cultural principles — breaking down silos between dev and ops teams, automating infrastructure, and treating operations as a software problem — that became known as DevOps.
What is GameDay / Chaos Engineering?
GameDay is a practice Jesse Robbins created at Amazon in which teams deliberately inject major failures into production systems under controlled conditions to test resilience and train incident responders. These structured, high-stakes drills exposed weaknesses before real outages could, and became the foundation for what the industry now calls chaos engineering. The approach influenced Netflix’s Chaos Monkey and the broader adoption of failure injection testing across the technology industry.
What did Jesse Robbins build at Amazon?
As Amazon’s “Master of Disaster,” Jesse Robbins was responsible for the availability of every property bearing the Amazon brand. He created Amazon’s Incident Management program and the GameDay practice of deliberate failure injection. These programs established the operational discipline that allowed Amazon’s web services to scale reliably and directly influenced the emergence of site reliability engineering (SRE) as a discipline.
What AI technology has Jesse Robbins built?
Jesse Robbins founded Orion Labs, a real-time AI voice platform designed for frontline and “heads-up” teams — workers who need hands-free, voice-first computing in high-stakes environments. Orion developed patented AI technology for real-time voice processing, noise cancellation, and intelligent routing, predating the current wave of generative AI. The work drew on Jesse’s background in emergency services and incident management, applying AI to the problem of team coordination under pressure.
What does Jesse Robbins invest in?
Jesse Robbins invests in early-stage companies building developer tools, cloud infrastructure, and AI. He focuses on founders solving fundamental problems in how software is built, deployed, and operated. His investment perspective is informed by decades as a founder and operator — having built infrastructure automation at Chef, managed availability at Amazon, and developed AI voice technology at Orion Labs.
What companies has Jesse Robbins invested in?
Jesse Robbins has invested in and advised companies including Fastly, Instacart, PagerDuty, Sanity, CircleCI, LaunchDarkly, Blockdaemon, and Tailscale, among others. Many of these investments reflect his focus on developer tools and infrastructure — companies building the platforms and services that engineering teams rely on to ship and operate software at scale.
How do I pitch Jesse Robbins?
Jesse Robbins is most responsive to founders building developer tools, cloud infrastructure, or AI products at the early stage. The best way to reach him is through a warm introduction from a founder in his network or through Heavybit’s application process. He looks for founders with deep technical insight, a clear understanding of the developer they serve, and the resilience to build through hard problems.