Sr. Operations Associate

Toronto, ON
Client Operations – Client Operations
Full-time

As a Sr. Operations Associate, you are responsible for identifying, prioritizing and driving key opportunities to enhance how our business runs, enable new strategic partnerships (e.g., carriers and others) and create infrastructure to serve different client structures. 

Your main objective will be to efficiently drive operations projects of different size and scope that create ongoing business impact. 

You will work closely with other operations associates, implementation project managers, client HR team members, carrier account managers, and product managers to (re)define business/product requirements and processes that impact our business end-to-end. 

Your mission is to explore the unknown, in order to chart a path for how League’s business evolves.

In this role you will

    • Define and drive projects that deliver measurable impact on League’s cost to serve or client experience, sometimes with support from an Operations Associate and other internal stakeholders, including: 
    • Understanding complex requirements, and designing and implementing processes to support them
    • Enhancing and documenting existing operational processes
    • Lead defining the end-to-end business process for new strategic partners and new product/service offerings, including: 
    • Support defining product requirements and rules in a scalable, agnostic manner
    • Mapping out and documenting key business processes
    • Aligning partners and external stakeholders to key business processes
    • Fostering relationships with external stakeholders
    • Contribute to defining the strategic direction of new strategic partnerships
    • Developing milestones and metrics to track the success of our partnerships
    • Develop systems to monitor key operational processes to track the effectiveness, quality and cost of operating our business
    • Develop processes to collect findings/insights for senior management to support key business decisions
    • Support running the day-to-day operations, including resolving our members’ and employers' most complicated inquires
    • Help shape the strategic direction and culture of a lean and mean operations team

Desired Outcomes

    • Delivery of operations projects
    • Enable League’s ability to deliver on new offerings
    • Enable League’s ability to serve increasingly diverse and sophisticated clients
    • Decrease the overall cost to serve
    • Improve the client experience

Required Education and Experience

    • 3+ years of work experience in a high-performance organization such as consulting, banking or a high-growth technology company
    • Demonstrated history of achievement and excellence
    • Previous SaaS / insurance / insurance administration experience are preferred
    • Bachelor’s degree (or equivalent)

Desired Attributes and Characteristics

    • Output and execution - With increasing independence, design and execute operational projects that deliver measurable impact
    • Project Management - Manage cross-functional projects with a high level of autonomy. 
    • Coaching & Feedback - Actively seeks and provides feedback graciously and learns from everything they do. Provides feedback on process development.
    • Flexibility and adaptability - Comfortable learning and defining the use of new software, programs, and processes.
    • Stakeholdering - Viewed by internal and external stakeholders as insightful, professional, effective and responsive. 
    • Collaboration - Work effectively and collaboratively with internal and external teams. 
    • Improvement - Will not settle for the status quo. Constantly identifying high impact opportunities to improve.
    • Strategic operative - Is able to understand and align detailed operations projects within the context of League’s strategic direction. 


We believe that diverse teams perform better, and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.