Staff Software Engineer

Staff Software Engineer Founding-level · Remote across Canada (Toronto-based team) · Healthcare SaaS Company Confidential — Canadian healthcare SaaS startup (~15 people) Role Staff Software Engineer — senior, founding-level; scope can flex to player-coach Location Remote anywhere in Canada · team is Toronto-based Reports to Head of Technology or the company’s leadership, depending on seniority Experience 5–20 years; calibrated to capability, not tenure Compensation Open depending on background ($150-210K ) + equity; bonus under consideration Stack Java / Spring Boot · React / TypeScript · MySQL · AWS Environment Healthcare / regulated — EMR integrations, PHI, SOC 2 · no dedicated QA THE OPPORTUNITY Our client is a Canadian healthcare SaaS startup that gives physicians back their time. Its platform manages the services OHIP doesn’t cover — forms, sick notes, prescription renewals — and handles the billing for them, fully integrated into the medical systems doctors already use. The traction is real: its first physician customers are live, and integrations with medical platforms, pharmacy systems and a major national retailer are in progress ahead of onboarding thousands of physicians over the next few months. The team is about 15 people, and this hire will shape the product and the platform at a moment when the architecture decisions really count. This is not a ticket-taker role. You won’t be waiting for specs — you’ll be helping write them. WHAT YOU’LL DO Own complex problems end to end — understand the business need, design the solution, build it and evolve it as the product grows.Lead integrations — medical platforms, EMRs, pharmacy systems and national retail partners, as the platform scales to thousands of doctors.Shape the product — sit in on product decisions and turn feature ideas into sound architecture: UI behaviour, APIs, domain logic, data model and infrastructure.Build with AI as a real partner — decompose work, write specs and prompts that produce high-quality output, and review AI-generated code rigorously.Raise the bar — with no dedicated QA, own quality in a regulated environment (PHI, SOC 2), and for the right person, grow into a player-coach or technical leadership role.WHAT WE’RE LOOKING FOR Three things matter most: product-to-architecture translation, systems thinking and design judgment, and AI-augmented execution. The pillars below show how candidates will be assessed. Fit Pillar Weight What Good Looks Like Product-to-Architecture Translation ★★★★★ Critical Takes a product description (not a technical spec) and walks it down alone: UI behaviour, API contracts, domain logic, data model, infrastructure. The hardest skill to find and the one AI can’t shortcut. Systems Thinking & Design Judgment ★★★★★ Critical Sees how a decision ripples: domain boundaries, coupling, what it does to the data model six months out. Makes the speed-vs-structure trade-off without hand-holding. AI-Augmented Engineering ★★★★★ Must-have Already coding with AI day to day (the team uses Claude Code). Decomposes work into delegable units, writes strong specs/prompts, and reviews AI output like a junior dev’s PR. Not currently using AI = not a fit. Ownership, Ambition & Startup Pace ★★★★☆ Strongly preferred Self-starting, wants a real say in product decisions and aspires to technical leadership (CTO trajectory). Startup or fast-moving environment strongly favoured. Integrations Depth ★★★★☆ Strongly preferred Owns third-party integrations end to end — medical platforms, EMRs, pharmacy and retail partners. Comfortable with messy external APIs and data mapping. Stack Alignment ★★★☆☆ Preferred Java / Spring Boot, React / TypeScript, MySQL, AWS. Strong engineers from adjacent stacks can be considered. Healthcare / EMR Experience ★★☆☆☆ Nice to have EMR integration (TELUS, Accuro), PHI handling, SOC 2 — a bonus, not a requirement. Also important: ambition and a desire for impact beyond a conventional developer role — this is a strong fit for someone who wants to be a CTO one day. Seniority is flexible (roughly 5–20 years); a less experienced engineer with exceptional capability can be considered, and a more senior player-coach could shape a newly created role. WHY THIS ROLE Real impact, early: a small team where your work is visible on day one and your input shapes the product.Proven demand: physicians already on the platform and major healthcare and retail integrations underway.Meaningful problem: giving physicians time back from admin and billing work.Ownership: competitive base, equity, and a genuine path to technical leadership.Flexibility: remote-first anywhere in Canada.