Backed by Y Combinator.
About the role
Your team. Hold a high bar and grow each engineer through direct, actionable feedback. Develop senior engineers into staff. Give clear priorities and expectations without adding process before we understand the problem. Hiring. Run hiring for your team, from sourcing to onboarding. You define the bar. 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 lead, part hiring engine. You'll start on a client engagement to learn the work and where engineers get stuck. Then you'll build and lead a team and help shape the company as we grow.
Your team. Hold a high bar and grow each engineer through direct, actionable feedback. Develop senior engineers into staff. Give clear priorities and expectations without adding process before we understand the problem.
Technical leadership. Review architecture, agent prompts and structure, and eval design. Step into the hardest technical and...
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