Backed by Y Combinator.
About the role
Your engineers. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech lead. Technical leadership. Review architecture, agent, prompt, and eval design on your engagements. Step into hard technical and client situations, like production regressions and unclear requirements, and make the call. Raise trouble early, while it's cheap to fix. Found on 1752vc Careers, the job board for startup and VC roles.
More about this role
Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems.
Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room.
This role is part player, part coach, part staffing partner. Most of your time stays on a client engagement, hands-on, close to the work and to where engineers get stuck. You'll manage a group of engineers across a few engagements and grow with the team as we do.
Level: Reports to the Head of Engineering. You run a team inside our system: you apply the bar, keep your engineers growing, and stay close to the work.
Your engineers. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech...
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