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Salary: CAD 140,000 - 182,200 / annual
League is a fast-growing healthcare experience platform serving 70+ million people through health plans and health systems (including Manulife, SCAN, Geisinger, Medibank, Baptist, and Shoppers Drug Mart). The company closes gaps in healthcare delivery by identifying what patients need to do next, removing barriers, and ensuring follow-through.
You will own League's design system end-to-end, serving web, iOS, and Android across all products and customers. This is a senior individual contributor role where you are measured by what other designers and engineers can build because of your infrastructure.
Key responsibilities:
- Own and evolve the design system: component authoring, theming architecture, and parity between design library and shipped code
- Own tooling between design and code, including token pipelines, plugins, and automated drift detection
- Build infrastructure enabling AI agents to use the design system correctly, including agent skills, reference documentation, and quality evals
- Ship production code into the design system and consuming surfaces
- Hold cross-platform constraints across web, iOS, and Android
- Set the accessibility bar so teams inherit it by default
- Own architectural decisions and drive them to resolution
- Document and teach AI workflows to improve the entire design practice
- Set craft standards through shipped work and build alignment across designers, engineers, and leads who don't report to you
League is an AI-native organization. You will use AI tools daily as part of your workflow, with demonstrated hands-on experience writing agent skills, wiring MCP servers, and benchmarking results. The company expects thoughtful leverage of AI to improve quality, speed, and impact of work.
Work location: Hybrid. League has a vibrant Toronto office. All Toronto-area employees (within 65 km of downtown HQ) collaborate in-office Monday–Thursday, with 10–20 flexible remote days per quarter depending on distance. Remote-eligible roles can be based anywhere in Canada or the US.
Compensation includes competitive base salary, performance-based bonus, stock options, unlimited paid time off, comprehensive health benefits (medical, dental, vision), spending accounts, wellness days, growth opportunities, mentorship, and flexible work arrangements.
REQUIREMENTS:
- 6+ years in a hybrid design/frontend role, frontend engineering, product design, or design engineering
- Portfolio of shipped work where you did both design and build
- Authorship of a design system (you'll be asked which decisions were yours, what you got wrong, and what you'd do differently)
- Strong design sensibility: care about craft, consistency, interaction quality; ability to articulate design decisions and tradeoffs
- Fluency in both halves: production React and TypeScript with strong component API design judgment; 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 MCP servers, and benchmarking results
- Account for real-world complexity: edge cases, empty and error states, accessibility, technical constraints
- High agency: pick up unowned work, form positions, drive to decisions
- Strong writing: much output is documentation read by designers, engineers, and agents
NICE TO HAVE:
- Native iOS or Android experience
- Tooling engineering in Node and TypeScript (CLIs, build scripts, token pipelines, CI automation)
- Server-driven UI development
- Health tech or regulated industry experience
- Experience designing evals or benchmarking AI output quality
