Senior jobs in Canada

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 League continues its rapid growth and seeks to revolutionize healthcare through technology, the strategic development and implementation of data products and AI solutions become paramount. We are seeking a highly motivated and experienced Product Management Leader to lead the strategy of our Data & AI platform.

You will spearhead high‑visibility, cross‑functional initiatives, fostering strong relationships with key stakeholders across the organization and the broader healthcare ecosystem.

The ideal candidate possesses a proven track record in leading the development of complex, scalable data environments, successfully launching data products, implementing AI/ML solutions, enabling data‑driven decision‑making, and shaping comprehensive data analytics strategies. With a strong background in leading high‑performing teams, this candidate will play a crucial role in guiding the innovative technologies/products to enhance our platform’s data environment and deliver personalized, AI‑powered experiences.

• Define Product Strategy & Vision: Lead and ensure cross‑functional alignment of our Data & AI platform strategy, ensuring it is meeting the needs of our portfolio of products & customers.
• AI Innovation: Advance League’s AI platform through experimentation and implementation of cutting‑edge technologies. Product management oversight of AI Health Story, guardrails, evaluation, MCP tools, and more.
• Personalization & Engagement: Drive strategy to ensure our platform offers personalized user experiences that meet the highest quality standards, leveraging AI and machine learning to maximize customer engagement and lifetime value.
• Grow a Team of High Performing Product Managers: Provide expert‑level coaching, mentorship, and feedback to support the product managers in your team; and ensure investments are exceeding our goals.
• Cross‑functional Leadership: Partner with peers in engineering, growth, customer strategy, and marketing to ensure platform products are leveraged appropriately and that their value is conveyed to internal and external leaders.

• A minimum of 7+ years of experience in data science product management, data product management, or AI/ML implementation - US healthcare industry experience preferred.
• A minimum of 3+ years of experience in progressively responsible leadership roles (through to the senior management level), managing medium to large‑sized teams and cross‑functional initiatives.
• Proven experience in building and launching successful data products from ideation to market.
• Strong understanding of AI/ML algorithms and techniques, with experience in applying them to real‑world business problems.
• Strong business acumen, with the ability to translate data insights and AI/ML models into tangible business value.
• Strong collaboration, communication, and interpersonal skills, with experience building positive working relationships with senior leaders across the business.
• Results‑driven and forward‑thinking, with the ability to influence and drive change across the organization.
• Excellent presentation and storytelling skills to communicate complex technical concepts to both technical and non‑technical audiences.

• 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.

• 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

$224,200 - $249,100 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 recruitinginfo@league.com.

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.

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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