Jesse Robbins

General Partner at Heavybit

Writes $500K – $5M checks · typically $2.5M

About

Jesse Robbins invests at the seed stage in AI developer tools and infrastructure, backing founders building tools and platforms developers depend on. He started out building ISPs in high school, had an early IPO in 1999, and stepped away from tech to train as a firefighter and EMT before joining Amazon in 2001, where he became "Master of Disaster" and created the GameDay practice that helped shape modern Incident Management, Site Reliability Engineering, and Chaos Engineering. After Amazon he cofounded the O'Reilly Velocity Conference and helped start the DevOps movement, then cofounded Chef, which he grew as founding CEO to $75M in revenue before it was sold; he later cofounded Orion Labs, a real-time voice AI platform for frontline teams. He has invested in and advised over 60 companies including PagerDuty, Fastly, Instacart, Sanity, and Blockdaemon, five of which have gone public, and works with founders at Heavybit as board member, advisor, and investor.

LinkedIn ↗X / Twitter ↗Website ↗Blog ↗

Invests in

AI & Machine LearningCybersecurityData & InfrastructureDeveloper ToolsEnterprise Software

Beyond investing

Founded: Cofounded Chef, the infrastructure automation company, and served as its founding CEO. Cofounded Orion Labs, a real-time voice AI platform for frontline teams. Cofounded the O'Reilly Velocity Conference with Steve Souders.
Communities: Helped start the DevOps movement.
Awards: Named to Business Insider's 2026 Seed 100 ranking of the best early-stage venture investors.
Hobbies: Trained as a firefighter and EMT after an early IPO in 1999.
More: Was building ISPs and working on early wireless modems in high school. Created the GameDay practice and chaos engineering at Amazon as 'Master of Disaster'.

From Jesse's own website — common ground for a warm intro.