Technical lead on enterprise AI engagements, owning work from discovery through production and acting as technical authority in client and sales conversations. Builds 0-to-1 systems and contributes to the internal Headstart Platform. Stack includes Python backend services, datastores, React/Next.js, and optionally ML; experience with agentic systems is expected.
About the company
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, a different problem, and a different set of constraints. You leave each one knowing that business deeply.
We are building our own platform, and have built our own coding agent Friday, which powers the majority of how we deliver. We're bootstrapped, cash-flow positive, and growing fast.
Why join us
Engineers who thrive at Headstart are builders who want to understand both how businesses and code works. We take the work seriously and the culture deliberately. Pay is transparent, weekends are yours, and we don't confuse long hours with good work.
About the role
Your background
What to expect
What we offer
This role offers extensive benefits, including:
If you’re NYC based — we have a loft office in Soho and provide lunch and snacks
While this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada.
Note: Even if you don't meet all the requirements, we still encourage you to apply.
Compensation: $265K
