Staff Software Engineer
Founding-level Staff Software Engineer at a ~15-person Canadian healthcare SaaS startup (remote anywhere in Canada, Toronto-based team). You'll own complex problems end to end, lead EMR/pharmacy/retail integrations, and shape architecture using Java/Spring Boot, React/TypeScript, MySQL and AWS, with AI-augmented workflows and quality ownership (PHI, SOC 2).
- Compensation
- Not disclosed
- Location
- Toronto, Canada
- Work setup
- Remote
- Seniority
- Staff
- Employment
- Not specified
- Experience
- 5+ years
- Category
- Software engineering
- Posted
Skills
Must have
- 5–20 years of experience, calibrated to capability rather than tenure
- Product-to-architecture translation
- Systems thinking and design judgment
- AI-augmented engineering: decomposing work, writing specs/prompts, reviewing AI-generated code
- Ownership, ambition and startup pace; self-starting with a say in product decisions
Nice to have
- Aspires to technical leadership (CTO trajectory); startup or fast-moving environment experience
- Integrations depth: third-party integrations end to end (medical platforms, EMRs, pharmacy, retail), messy external APIs and data mapping
- Stack alignment: Java / Spring Boot, React / TypeScript, MySQL, AWS
- EMR integration experience (TELUS, Accuro)
- PHI handling and SOC 2 experience
Full description
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
CompensationStack
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 FORThree 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.
WeightWhat Good Looks Like
Critical