About League

League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.

Position Summary:

League's platform enables our customers to offer highly engaging, personalized healthcare experiences to their members. As Product Manager, you will own defined problem spaces within our Member & Patient Portals and AI Agent Teams, spanning benefits navigation, care finding, messaging, scheduling, care gaps, and condition management. You'll operate the full PM role across 1–2 engineering pods with growing independence, working closely with a Solution Owner and Staff PMs to turn ambiguous problems into clear, outcome-oriented bets. This role is calibrated for someone early in their Product Management career (around 2 years of relevant experience) who is ready to own a scope independently while still building toward Senior PM.

In this role, you will:

Own problem framing and success metrics for defined bets within platform surfaces (e.g., benefits & claims, care finding, messaging, scheduling, Care Navigation Agent, Benefits Navigation Agent, Health Coach Agent, Care Gaps Agent)
Operate independently across 1–2 pods, growing toward full ownership of 2 pods over time
Bring domain signal and customer insight to your Solution Owner without being prompted; join upstream conversations on bet shaping
Define clear, scoped problem statements and outcome-oriented success metrics the pod can act on without needing to ask
Communicate bet intent clearly to your pod; spot and raise blockers, building the instinct to unblock without over-owning delivery
Surface when a bet's goal or box is at risk; escalate to Product Desk appropriately and distinguish delivery noise from bet-level signal
Build foundational knowledge of League's platform, digital provider and payer market, and the League AI product line; answer domain questions from your pod with growing confidence
Define KPIs, validate problem framing with data, and track bet performance against goals
Use AI tools (prompt engineering, research/synthesis, discovery prep) to accelerate bet framing, market research, and metric definition — use AI ethically and in line with League's data privacy policies
Contribute to interviews and onboarding for APM/PM-level hires as needed

About You:

2+ years of Product Management or related technology delivery experience
Interest in or exposure to digital healthcare; payer market experience is a plus but not required at this level
Comfortable operating with real ambiguity and turning it into a scoped problem statement and metrics without heavy hand-holding
Working knowledge of agile methodologies and comfort partnering with engineering and design in sprint ceremonies
Practical experience using AI tools for productivity (drafting, research, synthesis) and a genuine interest in building deeper AI fluency
Strong written and verbal communication skills — able to clearly explain trade-offs to your pod and Solution Owner
A track record of seeking feedback proactively and applying it quickly

Attributes & Characteristics

Clear, confident communicator and writer
Strong problem solver who distinguishes problems from solutions
Brings domain signal proactively rather than waiting for direction
Building foundational knowledge of League's platform, architecture, and the payer/digital health market
Comfortable with agile development processes
Creates space for teammates to contribute; listens with curiosity
Growth-minded — actively seeks feedback and coaching, and applies it visibly
Curious about and comfortable experimenting with AI tools in day-to-day PM work

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

$100,800—$126,000 CAD

AI Fluency & Ways of Working

At League, we are an AI-native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice:

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

How this scales by level:

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

What we look for:

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

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 [email protected].

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:

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.

Privacy Policy

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

Product Manager (platform & AI Agents)

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