Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.
Position Summary:
As a Principal Product Manager, you are the strategic architect of a sophisticated, high-scale platform for our Member Portal Solution for payer customers.
You are directly responsible for accelerating our 2026 growth trajectory and long-term AI-native vision. While we operate a robust digital infrastructure, we are at a pivotal moment of evolution—leveraging our high-scale foundations to drive an AI-native experience that is proactive, personalized, and dynamic.
Your mission is to drive the successful hardening of our core digital product capabilities while leading this strategic shift. This role requires a high degree of fluency in the US Payer landscape, claims data, and benefits orchestration. You will leverage the voice of the customer and deep healthcare market insights to inform our data-backed roadmap that prioritizes long-term margin expansion, TAM growth, and member experience quality. You will provide the strategic leverage required to de-risk delivery, mitigate architectural gaps before they become fires, and influence the Executive team with high-quality logic and roadmap rigor.
In this role, you will:
About You:
What we offer:
Security-Related Responsibilities
US APPLICANTS ONLY: The US-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 US 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.
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.
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