About the roleLead and own multiple client engagements end-to-end, from ideation and technical discovery through to productionPrototype rapidly while ensuring long-term reliability, maintainability, and securityBalance multiple concurrent engagements, context-switching between different technical stacks and business domainsContribute to the Headstart Platform roadmap by identifying and delivering the highest-leverage investments across our tooling and infrastructureShape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks likeBe the technical authority in sales and scoping conversationsGrow the engineers around you and raise the floor of every project you work onYour background7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-endBeen the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were toldExperience creatively applying AI in the development lifecycle, and knowing when not toEnjoys a fast-paced and cooperative environmentHave owned client relationships at the executive level: running discovery, navigating difficult conversations,



and earning trust quicklyProven full-stack depth: backend services (Python), datastores, React/Next.Js, optionally MLExperience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scaleBonus if you’ve been afounding 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 $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.Compensation Range: $240K#J-18808-Ljbffr

📌 Staff Software Engineer - $240,000 A Year (Winnipeg)
🏢 Headstart
📍 Winnipeg