When the servers go down,
he's been here before
In 2003, Jesse Robbins walked into an all-hands meeting at Amazon and proposed something unusual: let's intentionally break the website. Not because something went wrong - because carefully chosen, well-orchestrated failure teaches you things that success never can. He called it GameDay. His managers called it authorized. The rest of the industry, years later, called it chaos engineering.
Robbins grew up in Manchester-by-the-Sea, Massachusetts, and trained as a firefighter and EMT before any of the tech chapter happened. That's not a footnote to his career - it's the whole operating system. When you arrive on a fire scene, you don't debug the fire. You command the response. You stop the spread. You get people out. The instinct to act under uncertainty, to preserve core function while chaos burns around the edges, came from years of pulling hose and running calls before he ever wrote a line of runbook.
Amazon recognized the unusual package they'd hired. As Website Availability Manager, Robbins held formal responsibility for keeping all Amazon brand properties online - a role that eventually earned him the title "Master of Disaster," approved by management and printed without irony. By the time he left, he had contributed to a culture of deliberate resilience that would go on to influence Google, Netflix (hello, Chaos Monkey), Yahoo, and Facebook.
In 2007, with Tim O'Reilly, Robbins co-founded the Velocity Conference on Web Performance and Operations - at the time, a niche gathering for people who cared about whether websites stayed up. It grew into the place where a loose community of practitioners named and formalized what they were doing. The DevOps movement, as a recognized field with a philosophy and a vocabulary, traces a clear line back to Velocity.
Then came Chef. Co-founded in 2008 as Opscode with Barry Steinglass, Nathen Haneysmith, and Joshua Timberman, Chef was an open-source infrastructure automation framework that let engineers describe their server configurations as code. Apple, Facebook, Google, IBM, and Microsoft all ran it. Hundreds of thousands of developers used it. Progress Software acquired it in 2020 for over $200 million. The company spent a decade proving that infrastructure as code wasn't a clever idea - it was the only sensible way to operate at scale.
Robbins stepped back from the CEO role and into Chief Community Officer, then turned his attention to Orion Labs - a voice communication platform he co-founded with a fellow firefighter. The product, called Onyx, was described as a real-life Star Trek communicator: instant voice for teams, IoT devices, and field workers who needed to communicate without looking down at a phone. It was built by people who knew what it meant to need reliable, fast communication in a situation where fumbling with a touchscreen could cost you something.
Heavybit, the San Francisco venture firm focused exclusively on developer-first companies, had been in Robbins's orbit since 2014, when he joined part-time. When he went full-time in 2022, he brought a portfolio mind shaped by having lived the entire arc of modern developer infrastructure - from the early chaos of web operations to the emergence of DevOps to the cloud-native era to today's AI infrastructure moment.