About League League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side. Position Summary We’re building the next generation of intelligent, human-centered products that improve people’s health and well-being. We're looking for a Principal Design Engineer to own the bridge between design and code. Our design system serves web, iOS, and Android across every product and customer we support, which makes it the highest-leverage thing the design organization owns. You’ll own that system end to end: the component library, the theming architecture, the tooling that keeps design and code in sync, and the infrastructure that lets AI agents build with it correctly. This is a senior individual contributor role. The work is infrastructure, so you’ll be measured by what other designers and engineers can build because of what you built. In this role, you will: Own and evolve the design system: component authoring, theming architecture, and parity between the design library and what ships in code.



Own the tooling between design and code, including token pipelines, plugins, and automated checks that catch drift before people do. Build the infrastructure that lets AI agents use our design system correctly, including agent skills, reference documentation, and evals that measure whether the output holds up. Ship production code into the design system and the surfaces that consume it. Hold the cross-platform constraint across web, iOS, and Android, so one design decision serves all 3. Set the accessibility bar inside the system so teams inherit it by default. Own the open architectural questions about the system and drive each one to a decision. Document and teach your AI workflows so the whole design practice improves, not only your own output. Set the craft bar through what you ship, and build alignment with designers, engineers, and leads who don’t report to you. About You: 6+ years in a hybrid design/frontend role, frontend engineering, product design or design engineering, A portfolio of shipped work where you did both the design and the build. You’ve authored a design system. We’ll ask which decisions were yours, what you got wrong, and what you’d do differently. Robust design sensibility. You care about craft, consistency, and interaction quality, and you can articulate why a decision was right and what you traded away to get there. Fluent in both halves of the job: production React and TypeScript with real judgment about component API design, and Figma at authoring depth (variables, modes, component properties, design-to-code mapping). Daily, fluent use of Claude Code or equivalent, with hands‑on experience writing agent skills, wiring up MCP servers and benchmarking the results. You

📌 Principal Design Engineer (Toronto)
🏢 Portage Ventures GP
📍 Toronto