Senior Software Delivery Program Manager

Description:

League, founded in 2014, is the leading healthcare consumer experience (CX) platform powered by artificial intelligence (AI), serving more than 63 million people globally. With over $285 million raised in venture capital, League partners with top healthcare providers and organizations such as Highmark Health, Manulife, Medibank, and Shoppers Drug Mart to deliver personalized and impactful healthcare solutions.

As a Senior Software Delivery Program Manager, you will oversee multiple concurrent projects and workstreams to ensure seamless product implementations and efficient customer onboarding. This role requires strategic planning, cross-functional coordination, stakeholder management, and excellent communication skills. You will serve as the primary liaison between clients and League’s teams, ensuring deliverables are met on time and projects are executed with excellence.

Key Responsibilities:

• Act as a strategic partner for clients during onboarding, ensuring alignment and successful implementation.

• Develop and manage detailed project plans, risk logs, and status reports.

• Collaborate with cross-functional teams (engineering, product, marketing, operations) to deliver on client requirements.

• Manage program calendars, schedules, and meetings to ensure timely execution.

• Facilitate client discussions on implementation activities, risks, and escalations.

• Identify and mitigate project dependencies and risks to ensure delivery milestones are achieved.

• Support change control, governance meetings, and testing initiatives throughout the implementation lifecycle.

• Capture post-onboarding customer feedback and foster referenceable clients.

• Contribute to continuous process improvements, internal initiatives, and delivery model enhancements.

Qualifications:

• Bachelor’s degree or equivalent.

• 3–5 years in high-performance implementation roles.

• 5+ years of project management experience (preferred).

• Strong client-facing communication and problem-solving skills.

• Previous experience in healthcare, consumer apps, or technology industries.

What League Offers

• Comprehensive medical, dental, and vision benefits.

• Performance-based bonus program.

• Employee stock option program.

• Unlimited paid time off with wellness days.

• Tax-advantaged healthcare and dependent care spending accounts.

• Professional development, growth opportunities, and mentorship programs.

Security & Compliance Responsibilities

• Adherence to League’s Information Security Policies and secure coding practices.

• Responsible for incident reporting and compliance with company procedures.