About the company
Headstart https://www.headstart.nyc/ 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.
Why join us
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.
How we work
High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast.
- We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves.
- AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable.
- Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view.
- Breadth that compounds. You'll see more industries and problems in a year than most people see in a career.
- Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.