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Key skills for this role
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.
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.
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Toronto, CAN
Toronto, CAN
, CAN
Toronto, CAN
, USA
Toronto, CAN
Toronto, CAN
, USA
, USA
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.
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
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
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
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.
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
Healthcare platform company building consumer-centric digital front doors that empower people to live healthier lives through personalized and always-on health experiences.
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