Location
toronto
Job Type
Full-time
Posted
June 09, 2026
Job Description
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’ve built our own agent Friday, which powers the majority of how we deliver. We’re bootstrapped, cash-flow positive, and growing fast.
Why join us
The engineers who thrive at Headstart are the ones who want to understand how businesses work, not just how 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
- Own client engagements end-to-end, from technical discovery and scoping through to production
- Work directly with enterprise clients, translating ambiguous busin...