League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. That gap costs health plans and health systems money, and it costs people their health. Health plans and health systems trust us to do this at scale.

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.

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. 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. 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. Strong 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 account for real‑world complexity: edge cases, empty and error states, accessibility, and technical constraints. ~ Strong writing. Native iOS or Android experience.

Tooling engineering in Node and TypeScript: CLIs, build scripts, token pipelines, CI automation.

Experience designing evals or otherwise benchmarking AI output quality. Work at the frontier of design systems built for AI agents, where most of the prior art doesn’t exist yet. Set the technical direction for how design and engineering collaborate across 3 platforms.

Partner with a talented, cross‑disciplinary team of designers, engineers, and AI experts. Be part of a supportive, forward‑thinking design culture that values quality and experimentation. Competitive compensation, equity, and comprehensive benefits.

Flexible vacation and time‑off policy. Continuous learning and development support (courses, tools, reimbursements, etc.).

Comprehensive Health Benefits: We prioritize your well‑being with complete medical, dental, and vision coverage Bonus Program: Be rewarded for your contributions with our performance‑based bonus program Spending Accounts: Manage your healthcare and dependent care expenses with tax‑advantaged spending accounts Benefit from guidance and support from experienced leaders in your field Flexible Ways of Working: Compliance with Information Security Policies Compliance with League’s secure coding practice Responsibility and accountability for executing League's policies and procedures Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. 140,000—$182,200 CAD AI Fluency & Ways of Working At League, we are an AI‑native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality,



speed, and impact of their work.

Use AI tools as part of your daily workflow to enhance productivity, problem‑solving, and decision‑making (e.g., drafting, analysis, coding, research, or process automation) Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use Continuously learn and adapt as recent AI tools and capabilities emerge, incorporating them into your ways of working Identify opportunities to improve how work gets done from personal productivity to team‑level workflows by leveraging AI effectively Operate with strong data responsibility and security awareness , especially when working with sensitive or regulated information Individual Contributors: Use AI to improve personal productivity and quality of output Senior ICs / Managers: Integrate AI into team workflows and improve processes Drive AI adoption at the organizational level and shape how work is done across teams Demonstrated experience using AI tools in a practical, responsible way Ability to balance efficiency with quality and sound judgment We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We have a mix of office‑centric roles based in our vibrant Toronto office, and remote‑eligible roles based anywhere in Canada or US. Regardless of the role’s posted location, all Toronto‑area Leaguers (living within 65 km of our downtown HQ) collaborate in‑office Monday through Thursday.

Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep‑work time.

Highmark

Health, Google Cloud, League: new digital front door to seamless care Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors League raises $95 million USD in Series C to build world’s leading healthcare CX platform Forbes x League: The Platformization Of Healthcare Is Here Fast Company x League: If we want better innovations in healthtech, we need more competition Use of AI Notice League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.

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📌 Manager Design Engineering (Toronto)
🏢 Portage Ventures GP
📍 Toronto