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League

Senior Software Delivery Program Manager (Talent Pool Building - Toronto)

Hybrid

Toronto, Canada

Senior

Full Time

26-01-2026

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Skills

Communication Problem Solving Marketing Project Management Artificial Intelligence

Job Specifications

About League

Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart.

The Role

As Software Delivery Project Manager, you are responsible for managing multiple concurrent projects and/workstreams in a complex program to facilitate an efficient and successful product implementation and customer onboarding process, with minimal support and supervision.

Your main objective is to proactively and strategically manage new customer implementations, creating end-to-end project plans, facilitating the execution of deliverables, keeping stakeholders informed of status and risks, coordinating actions with internal departments to fulfill client needs, and tracking progress against plan. It is vital to have strong customer facing communication skills and an ability to identify and escalate barriers to project success. You will act as a primary liaison between our customer and League's cross-functional teams. You will be required to manage both technical and non-technical discussions, including clear articulation of issues and risks that arise and translate those issues and risks into actionable deliverables and oversee their resolution.

In This Role, You Will

Act as a strategic and trustworthy partner between your client and League during the onboarding process
Accountable for the creation and management of one or more project plans, status reports, and risk and issue logs
Manage program calendar and meeting schedule to track towards timely execution of implementation
Collaborate with a cross functional team, during a project to inform various stakeholders of upcoming tasks, project status and escalating issues when necessary
Demonstrate the ability to motivate and guide internal teams to deliver according to plan, including but not limited to:
Marketing and Communication teams in regards to communications and engagement strategy
Product and Engineering teams for discovery meetings and delivering to customer requirements
Operation teams to ensure proper processes are in place post launch
Lead client discussions on implementation and/or project activities
Demonstrate core problem solving skills to support the delivery of a successful implementation and product development when faced with uncertainty
Support identifying dependencies and coordinating with your cross-functional teams to ensure attainment of dependencies and mitigation where appropriate to ensure delivery scheduled adherence
Support change control processes and governance meetings to ensure alignment and integrity of the project scope and timeline
Support Testing initiatives across the implementation lifecycle and act as the liaison with the customer for League's testing resources
Proactively reach out to clients & decision makers to manage expectations and drive accountability
Manage deliverable and document control process throughout implementation phases
Capture ongoing and post-onboarding customer feedback, and initiate CSAT survey to contribute to Implementation Team’s ongoing process enhancements
Foster referenceable clients who are openly willing to speak about their onboarding experience
Project management best practices and apply tools and processes per internal standard
Partner with Delivery Lead to communicate and escalate barriers to ensure project success
Support internal initiatives to develop or improve documentation and processes that contribute to League’s delivery model

About You

3-5 years experience in a high-performance implementation capacity
5+ years of project management experience preferred
Bachelor’s degree or equivalent
Experience in the healthcare, consumer applications or technology required

What We Offer

Comprehensive Health Benefits: We prioritize your well-being with complete medical, dental, and vision coverage
Bonus Program: Be rewarded for your contributions with our performance-based bonus program
Employee Stock Option Program: Become an owner and share in our success through our stock option program
Unlimited Paid Time Off: Take the time you need to recharge and maintain a healthy work-life balance
Spending Accounts: Manage your healthcare and dependent care expenses with tax-advantaged spending accounts
Wellness Days: Prioritize your mental and physical health with dedicated wellness days throughout the year
Growth Opportunities: We invest in your future with abundant opportunities for professional development and advancement
Mentorship Program: Benefi

About the Company

Founded in 2014, League is a platform technology company powering next-generation healthcare consumer experiences. Payers, providers, consumer health partners and employers build on League’s platform to deliver high-engagement, personalized healthcare experiences consumers love. Millions of people use solutions powered by League to access, navigate and pay for care. Know more