Full-Time Anywhere

Help Us Shape the Future of Healthcare

At League, we’re big on building connections – both through our product and with each other. Our platform is consumer-centric, personalized, and always on. It’s a front door to healthcare that empowers people to live healthier, happier lives. Every day.

When you feel connected to our mission, values, and the work you do, you’re driven to perform your best every day. When you feel connected to people you work with, you’re able to build meaningful relationships that last. Together, we share the ultimate goal of delivering better health outcomes for everyone.

The world has changed, and so has the way we work. We believe you can work where you work best (whether it’s in the office all the time, a few days a week, or none of the time), and still feel connected to our mission, values, purpose, and each other.  League is headquartered in Toronto with a second office in Chicago and we believe in empowering Leaguers to work their way—anywhere that works for them in Canada and the US.

All Leaguers have League life moments – moments in our careers that connect us to League’s mission and values, to each other, and to our amazing work – every day.

This role permits you to work remotely from any city in the United States or Canada.

League’s platform is highly engaging, digital-first, and always at your fingertips. On the product management team at League, you will tackle extremely challenging problems in the complex health care and benefits space, with the ultimate goal of delivering better health outcomes for everyone. We are open to product managers and senior product managers and have spots on several of our teams. Get to know us and let us know if your skills and interest can help us on our mission to help people be healthier!

Product Teams
Health Team Mission: Our health teams have set out to provide a highly personalized, digital experience for all members of our platform. Through virtual care, health programs, personalized health profiles, and access to products in the marketplace, the health teams deliver an exceptional, consumer-first product.

Benefits Team Mission: Our benefits teams are driven by helping our members understand and engage with their Employer-provided benefits more actively and effectively. For our customers, continuously deliver value by providing a leading benefits administration experience across many complex benefits plans and offerings.

Role of Product Management @ League

  • Continuously evaluate and prioritize new feature builds with a view on customer and business impact.
  • Define, prioritize and execute annual and quarterly roadmaps to maximize value to our customers and the business.
  • Drive alignment across business stakeholders, engineering and product design to ensure that the right product outcomes are delivered.
  • Define success metrics, ensure constant measurement, and iterative product build to drive measurable impact on key customer and business metrics.
  • Define, execute and optimize the business impact of your product area and how it relates to overall business KPIs.
  • Set KPIs with your squad that drives overall business impact.
  • Communicate business impact to team, stakeholders, and the company.
  • Effectively lead a cross-functional team while inspiring the team to get buy-in.
  • Advocate for the product roadmap to ensure alignment and high impact on priorities.
  • Regularly set context and empower others to make decisions through strong communication.
  • Actively coach and mentor those in their squad as well as other members of the product team.
  • Translate and identify technical limitations with ease and have an understanding of development effort. Effectively prioritize tech debt, and help developers understand tradeoffs.
  • Highlight technical risks and help inform architecture decisions by providing product vision context.

Attributes of Product Managers @ League

  • You have previous experience leading cross-functional product squads in a fast-moving agile environment – experience in scrum/kanban is an advantage.
  • You can easily demonstrate the business and customer impact that previous products you shipped have made.
  • You are a strong communicator and can break complex concepts into simple digestible pieces of communication, good at working with a diverse set of stakeholders.
  • You are a strong problem solver with a bias for action and a “get it done” mentality.
  • You are metrics-driven and think quantitatively, very comfortable with uncertainty and always looking to make data-driven decisions.
  • You share big & bold ideas and consistently display a figure-it-out mentality.
  • You embody and promote League’s values and mission.
  • You recognize and reward the efforts and contributions of others.
  • You advocate for the health & wellbeing of others.
  • You invite others (with different perspectives and backgrounds) to share ideas and come up with the best possible solution.
  • You learn quickly from experiences and are not afraid to make mistakes.
  • You display a high level of intellectual curiosity across subjects/fields.

Product Management Levels

Product Manager: In this role, you will drive a specific area of the product with a cross-functional squad, in order to execute on the product roadmap.

Senior Product Manager: In this role, you will own complex areas of the product that are interconnected with a squad of engineers and product designers, in order to execute on the product roadmap.

Product Management Lead: In this role, you will own an entire product line, set the long-term strategy, enable the product teams to execute on the product roadmaps. Manage and mentor a team of PMs at all levels.

At League, everyone is welcome. Diversity makes us better, and we believe in building diversity across cultural identity, gender, sexual orientation, age, and education, thought, and experience.

We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.

Here are some additional resources to learn more about League:

Tagged as: Flexible hours, Remote