Senior Manager Customer Success

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.

Will your first League life moment be meeting our team? We can’t wait to meet you.

As Senior Manager Customer Success you will work as part of the Customer Success team to ensure League is delivering a best-in-class experience to our customers. The Senior Manager’s mission is to help our customers’ employees live happier, healthier lives every day.

As Senior Manager, you will report to the AVP of Customer Success. You are responsible for supporting the operational and strategic execution and service delivery for League’s customers.  Responsibilities include supporting the AVP in the management and operations of the E3 service model, with an emphasis on achieving team KPIs & SLAs, coaching, and supporting the development and training of team members, operationalizing strategic objectives, and interacting with customers as a point of escalation to ensure an exceptional customer experience. The ideal candidate will possess a commitment to League’s core values, a commitment to life-long learning, a passion for problem solving and strategic thinking, and a deep belief in the power of League to impact the lives of those we serve.

In the Senior Manager role, you will:

  • Responsible for the day-to-day operations of a team of Customer Success Managers/Analysts & Customer Success Specialists
  • Acts as the point of escalation for any customer or team issues
  • Responsible for driving team towards team KPIs and SLAs
  • Manage and ensure team members are following best practices, policies, procedures and adhering to compliance regulations
  • Provide coaching, mentoring, development, and training to CS team members
  • Conducting internal facing training to enable our  team to confidently use and speak to League tools.
  • Source, screen and interview candidates for the Customer Success team
  • Conduct regular one-on-ones with Customer Success Managers/Analysts and Customer Success Specialists reporting into you
  • Report weekly on E3 performance, and SLA adherence to the AVP of Customer Success
  • Perform regular QA on team member’s cases and queues, ensuring consistent quality and providing ongoing feedback
  • Establish effective and positive communication amongst all team members
  • Work closely with the Customer Care and Customer Success Teams to identify trending customer inquiries
  • Take initiative to recommend and implement quality processes and process improvements
  • Troubleshoot and resolve customer issues with the team when necessary
  • Any additional responsibilities assigned


  • Strong leadership skills and a drive to make a large impact on the company, our team and our customers
  • Strong business and technical acumen, and executive presence, combined with deep analytical and organizational skills; strong understanding of value drivers in recurring revenue business models
  • Confident, capable, enthusiastic self-starter with minimal need for direction
  • Strong planning and multi-tasking skills and demonstrated ability to meet multiple and conflicting demands and deadlines
  • Results-oriented individual with a history of setting and attaining goals and meeting aggressive timelines
  • Passion for data, analytics, and process: ability and desire to dive into data to understand metrics
  • Clearly articulate your thoughts and ideas to present information in a straightforward and logical way
  • Can identify problems or gaps proactively and address them with lucrative solutions

Required Education / Certificates / Experience

  • BA, MBA or equivalent
  • Experience in benefits, insurance, health IT or SaaS preferred

You are:

  • Someone who loves to win and hustles to ensure success; you thrive in a fast-paced environment, and you don't fade under pressure
  • A person dedicated to exemplary customer satisfaction; the customer comes first and you are committed to ensuring the very best service and support
  • A life-long learner; you prioritize learning and development and want to get better everyday
  • An advocate; you have passion for health, wellness and driving innovation
  • A strategic thinker; you have an analytical mind and can overcome challenges, on-the-fly, in a thoughtful and meaningful way
  • A team player; you understand that Customer Success is a team sport and, in order to build something special, we need to make each other better
  • Someone who loves working with a team and fostering positive and healthy relationships
  • Someone who has grace under pressure and is comfortable with ambiguity, change and growth

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:

Learn more about us in this short video!

League, Cleveland Clinic collaborate to make employees healthier across North America

League and Loblaw bring next-generation digital health platform to customers

League Completes Workday Approved Integration

Given the current public health guidance on COVID-19 and to help support office health and safety, at this time, it is our company policy to require all Leaguers to be fully vaccinated to attend our offices in person.

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