Senior Software Delivery Program Manager; Talent Pool Building

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 dollars 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.

As Senior Software Delivery Program Manager, you are responsible for managing multiple concurrent projects and work streams 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.

• 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 and 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 elevate barriers to ensure project success
• Support internal initiatives to develop or improve documentation and processes that contribute to League’s delivery model

• 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…