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

The 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

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)

- Adaptable time off

📌 Product Manager (Toronto)
🏢 League
📍 Toronto