Product Manager, League
Platform & AI Agents
CA$100.8-126k
+ Bonus & Equity
Consumer experience platform for healthcare
Be an early applicant
Consumer experience platform for healthcare
501-1000 employees
Be an early applicant
CA$100.8-126k
+ Bonus & Equity
501-1000 employees
Company mission
To power next-generation healthcare experiences with a platform built to enable CX transformation.
Role
Who you are
- 2+ years of Product Management or related technology delivery experience
- Exposure to AI Platforms, no-code agent builders and frontier models, etc
- 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
- 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
- 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
What the job involves
- League's platform enables our customers to offer highly engaging, personalized healthcare experiences to their members
- As a Product Manager II, 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 PM career (around 2 years of relevant experience) who is ready to own a scope independently while still building toward Senior PM
- 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
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
Our take
Health benefits are a top requirement for anyone seeking a new job in the US today, but classic one-size-fits-all plans are no longer regarded fit for service. League's platform - for payers, providers, consumer health businesses, and employees - connects all benefits in one HIPAA-compliant place, to enable all bodies involved with health benefits to provide better customer healthcare experiences.
League is already one of the bigger players in the employee wellness space, having capitalised on the recently accepted correlation between employee health and productivity to secure huge clients like Uber, Shopify and Unilever. The company has seen significant investment, which will support the scaling of its platform-as-a-service offering. With more than 63 million contracted users, it is securing its position as the leading digital infrastructure for an integrated health ecosystem.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Feb 2022
$95m
SERIES C
Jul 2018
$47.1m
SERIES B
Total funding: $171.1m
Company benefits
- Flexible medical and dental plans
- 401(k) and RRSP matching programs
- Health, lifestyle, learning and family spending accounts
- Employee stock option program (ESOP)
- Generous leaves (including parental and sabbatical)
- Flexible time off
Company HQ
Entertainment District, Toronto, ON
Leadership
Michael Serbinis
(Founder & CEO)Founder of DocSpace and Kobo. Experience as CEO for Three Angels Capital and Board Director for Vector Insitute, among other prominent business leadership roles.
Salary benchmarks
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