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. - 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. - High agency. You pick up unowned work, form a position, and drive it to a decision. - Strong writing. Much of your 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 another regulated industry. - Experience designing evals or otherwise benchmarking AI output quality. Why you should join - Own the system that every team and every product at League depends on. - 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. - Join a fast-growing company redefining the future of healthcare experiences. - 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.). What we offer - 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 - Employee Stock Option Program: Become an owner and share in our success through our stock option program - Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance - Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts - Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year - Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement - Mentorship Program: Benefit from guidance and support from experienced leaders in your field - Flexible Ways of Working: Enjoy the freedom to work in a way that suits your life and boosts your productivity Security-Related Responsibilities: - 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. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. 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. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process. Compensation range for Canada applicants only $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. What this means in practice: - 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 new 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 How this scales by level: - Individual Contributors: Use AI to improve personal productivity and quality of output - Senior ICs / Managers: Integrate AI into team workflows and improve processes - Leaders: Drive AI adoption at the organizational level and shape how work is done across teams What we look for: - Demonstrated experience using AI tools in a practical, responsible way - Curiosity and openness to experimenting with new technologies - Ability to balance efficiency with quality and sound judgment Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you. 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. If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com. Our Application Process: Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps - You should receive a confirmation email after submitting your application. - A recruiter (not a computer) reviews all applications at League. - If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring. - The final step is an offer, which we hope you will accept! - Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring. Here are some additional resources to learn more about League: - Learn about our platform, leadership team and partners - 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 Work Location: We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. 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. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location. Recognize and Avoid Employment scams. Practice safe job searching. Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here. Use of AI Notice We are committed to ensuring fairness and transparency throughout our hiring process. 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. Privacy Policy Review our Privacy Policy for information on how League is protecting personal data.

Principal Design Engineer

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