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.
The engineers who thrive at Headstart are the ones who want to understand how businesses work, not just how code works. We work inside real enterprises, shipping production AI systems that change how they operate. 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 roleLead and own multiple client engagements end-to-end, from ideation and technical discovery through to production
Prototype rapidly while ensuring long-term reliability, maintainability, and security
Balance multiple concurrent engagements, context-switching between different technical stacks and business domains
Contribute to the Headstart Platform roadmap by identifying and delivering the highest-leverage investments across our tooling and infrastructure
Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like
Be the technical authority in sales and scoping conversations
Grow the engineers around you and raise the floor of every project you work on
7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-end
Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told
Experience creatively applying AI in the development lifecycle, and knowing when not to
Enjoys a fast-paced and collaborative environment
Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly
Proven full-stack depth: backend services (Python), datastores, React/Next.js, optionally ML
Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale
Bonus if you’ve been a founding engineer or startup early hire, with history building production products from scratch
Bonus if you’re NYC based — we have a loft office in Soho and provide lunch and snacks
Note: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $240,000 USD plus competitive equity compensation, 401k with employer match, fully covered medical, dental, and vision premiums, monthly wellness stipend, free lunch everyday in our NYC office, Citi Bike + pre-tax commuter benefits, and 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.
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 for the right fit.
Headstart AI Toronto, Ontario, CAN Office
Toronto, Toronto, ON, Canada
