Staff Software Engineer

Staff Software Engineer
Remote-first within Canada · Toronto-based · Healthcare / regulated

ABOUT DOCNOTE
Docnote is an early-stage Canadian health technology company reinventing how uninsured medical services are delivered. Physicians aren’t compensated by provincial health insurance for tasks like sick notes, medical forms, disability tax credit applications, and prescription renewals — so these fall on clinics as unpaid administrative work. Docnote provides an end-to-end platform that manages the entire process, from the initial patient request through to secure payment collection and digital document delivery, integrating with existing EMR systems.
The company’s mission is to eliminate administrative burden from the practice of medicine — giving physicians the tools to run a sustainable, modern clinic while offering patients a dignified, transparent experience. Docnote is currently operating in Ontario with an early-revenue, product-market-fit focus and a national expansion strategy.
What We’re Looking For
This is a high-autonomy role for someone who can own complex problems end-to-end: understand the business need, design the solution, build it, and evolve it as the product grows. This is not a ticket-taker role. You’re not waiting for specs — you’re helping create them.
There are three things that matter most for this role.
1 Product-to-Architecture Translation
The ability to take a product requirement — not a technical spec, a product description — and walk it all the way down on your own: UI behavior, API contracts, domain logic, data model, and infrastructure. This is the person who hears a feature description and immediately sees the full technical picture without being told what to build. It’s the hardest skill to find and the one AI can’t shortcut.
2 Systems Thinking and Design Judgment
The ability to see how a decision ripples across the system. Not just solving the immediate problem, but understanding what it does to your domain boundaries, whether it creates coupling you’ll regret, and how it affects the data model six months from now. This person makes the right trade-off between speed and structure without hand-holding. AI can generate code all day. It can’t tell you whether you’re building the right abstraction.
3 AI-Augmented Execution Fluency
Comfort working with agentic AI as a real development partner, not just autocomplete. This means decomposing work into well-scoped, delegable units, writing specs and prompts that produce high-quality output, and reviewing AI-generated work with the same rigor you’d apply to a junior developer’s PR. This skill is learnable if the first two are already there.
The Stack
BACKEND
Java / Spring Boot
FRONTEND
React / TypeScript
DATABASE
MySQL
INFRASTRUCTURE
AWS

Work arrangement
Yes