Principal Product Manager

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.

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.

• Serve as the subject matter expert for US Healthcare integrations, with a primary focus on helping members navigate the complexities of the healthcare system—specifically demystifying EOBs, claims status, accumulators, and complex benefits.
• Drive the product strategy for administrative self‑service, ensuring members can easily take care of necessary actions and understand their financial and health data without friction.
• Synthesize complex member needs and market dynamics into a solidified, roadmap focused on new revenue generation and efficiency.
• Create buy‑in for the product strategy with the Product Leadership Team through high‑quality logic and rigorous business‑case storytelling.
• Define and execute a roadmap to increase the utilization of key features, proving that users can successfully complete their intended tasks and derive tangible value from the portal.
• Ensure cross‑functional alignment across the 'Triangle' (Product, Engineering, Design) to eliminate silos to the Essential Duties.
• Define goals & measure success for the portfolio.
• Represent our platform and infrastructure externally with clients and prospects.
• Establish and deliver a high‑integrity roadmap built to ensure predictable, high‑scale execution, characterized by vetted trade‑offs and binary commitments.
• Significantly expand member reach and engagement. Accelerate program enrollment, feature adoption, and task completion rates through optimized member journeys, delivering measurable ROI for payer customers.
• Drive industry‑leading utilization and accuracy across core member domains including coverage, cost, claims, and accumulators, ensuring seamless member access to their financial and health data.
• Optimize the home screen and overall information architecture (IA) of the Member Portal to ensure the experience is optimized for discoverability, findability, self‑service, and ease of use.
• Successfully transition AI prototypes into production‑grade experiences that redefine the member experience and achieve market readiness.

• 6+ years in Product Management with a minimum of 3 years specifically in the US Payer or Health Insurance space.
• Proven ability to move an organization through architecting rather than individual output.
• Experience working at a platform company or leading the implementation of complex platforms. You have deep experience in agile methodologies—leading agile release…