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. 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 Senior Software Delivery Program Manager

– Manage multiple concurrent projects and workstreams in a complex program to facilitate efficient and successful product implementation and customer onboarding with minimal support and supervision.

Act as a strategic and trustworthy partner between clients and League during the onboarding process.

Accountable for creating and managing one or more project plans, status reports, and risk and issue logs.

Manage the program calendar and meeting schedule to track timely execution of implementation.

Collaborate with a cross‑functional team throughout the project to inform stakeholders of upcoming tasks, project status, and to elevate 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 – communications and engagement strategy.

Product and Engineering teams – discovery meetings and delivery to customer requirements.

Operations teams – ensuring 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 cross‑functional teams to ensure attainment of dependencies and mitigation where appropriate to maintain scheduled delivery.

Manage change control processes and governance meetings to ensure alignment and integrity of 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 and decision makers to manage expectations and drive accountability.

Manage deliverable and document control processes 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.

Apply project‑management best practices and mandatory tools and processes per internal standard.

Partner with Delivery Lead to communicate and elevate 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 sector required.

What We Offer

Comprehensive Health Advantages

– complete medical, dental, and vision coverage.

Bonus Program

– performance‑based bonus program.

Employee Stock Option Program

– opportunity to share in League's success.

Unlimited Paid Time Off

– recharge and maintain a healthy work‑life balance.

Spending Accounts

– manage healthcare and dependent care expenses with tax‑advantaged accounts.

Wellness Days

– dedicated days for mental and physical health each year.

Growth Opportunities

– abundant opportunities for professional development and advancement.

Mentorship Program

– guidance and support from experienced leaders.

Security‑related Responsibilities

Compliance with Information Security Policies.

Compliance with League's secure coding practice.

Responsibility and accountability for executing League's policies and procedures.

Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations.

Compensation Compensation range for Canada applicants only: $111,500—$139,400 CAD.

Equal Employment Opportunity We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or veteran status. If you need assistance during our recruitment process, please contact [email protected].

#J-18808-Ljbffr

📌 Senior Software Delivery Program Manager (Toronto)
🏢 League
📍 Toronto