About the companyHeadstart 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 usThe 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 roleOwn client engagements end-to-end, from technical discovery and scoping through to productionWork directly with enterprise clients, translating ambiguous business problems into concrete technical scopeShip production AI systems across multiple domains and stacks: agents, LLM workflows, document processing, and the infrastructure that makes them reliableContribute to Friday and the Headstart Platform via patterns, skills, and infrastructure that compound across every engagementRaise the bar for the engineers around you through code review, pairing,



and shared standardsYour background5+ years of engineering experience with a track record of owning systems end-to-endComfortable in client-facing situations, running discovery, earning trust quickly, and shaping what gets builtYour instincts and standards are contagious and teammates adopt them naturallyYou use AI tools constantly, creatively, and with good judgment about when not toProven full-stack depth: backend services (Python), datastores (SQL/NoSQL), optionally React/Next.JsExperience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scaleBonus if you've been a founding engineer or startup early hire, with history building production products from scratchBonus if you're NYC based — we have a loft office in Soho and provide lunch and snacksNote: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $200,000 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 perks, 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.#J-18808-Ljbffr

📌 Senior Software Engineer - $200,000 A Year (Toronto)
🏢 Headstart
📍 Toronto