Principal, Product Management

About League

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:

League's platform enables organizations to deliver highly engaging, personalized digital healthcare experiences. As a Principal Product Manager in the Client Solutions organization, you will play a critical role in shaping, delivering, and evolving client-facing digital health solutions built on League's platform.

This role is designed for a senior, externally facing product leader who combines deep product management expertise with a strong understanding of the digital healthcare ecosystem. You will partner closely with clients, customer strategy teams, engineering, design, and platform product teams to translate complex healthcare needs into scalable, high-impact product solutions.

You will be accountable for defining product strategy and roadmaps for client solutions, leading discovery and delivery of custom and configurable capabilities, and ensuring successful outcomes for external healthcare clients operating in regulated, complex environments.

In this role, you will:

Product Strategy & Roadmap

• Own and evolve the product strategy and roadmap for client-facing digital health solutions built on the League platform
• Identify opportunities to deliver differentiated value through new capabilities, integrations, and optimizations
• Balance client-specific needs with platform scalability and long-term product vision
• Clearly articulate product direction, priorities, and trade-offs to internal and external stakeholders

Client-Facing Product Leadership

• Serve as the primary product management partner for external clients
• Lead product discovery with client stakeholders to deeply understand business goals, user needs, and healthcare workflows
• Translate client requirements into clear product requirements, value propositions, and success metrics
• Manage expectations and ensure alignment across clients, internal teams, and leadership
• Spend meaningful time working directly with clients (including occasional on-site engagement)

Delivery & Execution

• Own and prioritize the product backlog for client solutions, ensuring focus on highest-impact outcomes
• Partner with engineering, design, and delivery teams to drive execution through agile practices
• Actively participate in agile ceremonies, release planning, and iterative delivery
• Monitor product performance and client outcomes, using data and feedback to drive continuous improvement

Cross-Functional Collaboration

• Work closely with Customer Success, Sales, and Implementation teams to support successful client onboarding and ongoing value realization
• Collaborate with platform product teams to influence shared capabilities and platform evolution
• Act as a thought leader for digital healthcare product best practices within the organization

About You:

• 8+ years of experience in Product Management or digital product delivery, with at least 3–5 years in senior or principal-level roles
• Demonstrated experience delivering digital healthcare products (e.g., health platforms, care navigation, benefits, provider tools, health data, or regulated consumer health solutions)
• Expert in modern product management practices, including discovery, roadmap development, and outcome-driven delivery
• Working knowledge of native/cross-platform mobile development frameworks and Web front-end frameworks (React, Angular, etc.)
• Proficient in measuring product performance, and experience working with product analytics tools (Pendo, Amplitude) and business intelligence platforms (Looker) 
• Strong agile practitioner with experience leading iterative, value-driven delivery
• Exceptional communication, presentation, and stakeholder management skills
• Ability to influence without authority and lead through collaboration
• Confident engaging with senior client stakeholders and internal leadership
• Experience conducting A/B testing and designing experiments to evaluate solution performance and quantifiable behaviour change an asset

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

Security-Related Responsibilities

• Ensure access management is performed in compliance with the employee's role and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/ team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations
• Compliance with Information Security Policies

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

$142,200 - $177,500 CAD

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

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.

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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.

Review our for information on how League is protecting personal data.

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