Staff Software Engineer

4 weeks ago

Toronto, Canada Headstart AI Full time

Staff Software Engineer at Headstart AI Base pay range: $235,000.00/yr – $235,000.00/yr About the Company Headstart AI’s mission is to bring companies into the age of intelligence and automate software development. We are the team behind the coding agent Friday and are building frontier applied AI technologies including agent orchestration, memory, and more. We specialize in solving problems with the latest LLM capabilities that deliver measurable outcomes and breakthrough results for organizations across many industries, providing custom software solutions and a suite of tools to stay ahead of the intelligence curve. About the Team We are a lean, high‑velocity team that ships breakthrough AI capabilities at startup speed. Working directly with our users, we iterate rapidly and measure success by the real‑world impact we create for our clients. Simplicity and engineering fundamentals are more important than ever in an AI‑driven world. About the Role Lead and own 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 Establish scalable architectural patterns, frameworks, and technical standards that are repeatable and accelerate delivery across multiple projects Build relationships with technical and business stakeholders and identify strategic opportunities within client relationships Participate in sales and product processes by providing technical credibility and architectural context to help scope work and close deals Mentor and support the growth of other engineers while helping to define and drive the technical roadmap Your Background 7+ years of professional software engineering experience Strong interest in leveraging AI in the development lifecycle (bonus if experience) Enjoys a fast‑paced and collaborative environment Exceptional communication skills with the ability to explain technical concepts to non‑technical audiences and build trust within internal team and with external clients Proven track record owning full‑stack systems: backend services (Python, FastAPI, Node.js), relational databases (Postgres/MySQL), and optionally frontend frameworks like React/Next.js 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 Benefits Even if you don’t meet all the requirements, we encourage you to apply. This role offers extensive benefits: a base salary of $235,000 USD plus competitive equity compensation, 401k match, paid time off, health and dental insurance, and a dynamic, innovative work environment. Other Information Seniority level: Mid‑Senior Employment type: Full‑time Location: Remote with optional NYC office #J-18808-Ljbffr

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