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Principal, Delivery

League Inc.
CompanyLeague Inc.
CategoryOperations & Admin
LocationCanada
RemoteOn-site (inferred)
EmploymentNot stated
LevelDirector
SalaryNot stated by the employer
Posted7 May 2026
Last verified4 Aug 2026
SourceEmployer ATS (greenhouse)
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Description
About League   League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side.  The Role  As Principal, Delivery, you are accountable for meeting customer deliverables as per contractual agreements (scope and time), and internal budget. The ideal candidate will drive and guide disciplined execution through the use of consistent methodologies, processes, and strong communication skills. You will be a passionate advocate for the League product and ensure the platform is implemented on time and with high quality to meet our clients’ business needs. In this role, you are expected to: Manage, lead and oversee one or more client implementations and internal company and/or team initiatives simultaneously Implement the project governance structure, including delivery structure, change control and processes to support risk and issue escalation, decision making and program status  Lead the organization and deployment of League resources for implementation, the production of deliverables, and the oversight of timelines to ensure a seamless delivery of League products to clients Accountable for build and maintenance of end to end integrated program plans, resource assignments, budgets and performance against targeted implementation milestones for the implementation and teams Serve as escalation point for risks, issues, and decisions one or more implementations simultaneously Maintain a deep understanding of League’s product and platform to inform key business requirements and decisions during implementations Lead internal teams and the client on a successful change management plan by creating deliverables based on client pain points and objectives Collaborate on communication plans and drive accountability for obtaining final approvals on client deliverables Develop and manage a high performing team by providing direction and guidance both on the job and as a career coach to Implementation team members Coach and develop staff to have a deep understanding of implementation delivery methodology and the League’s product and platform Lead key internal initiatives to drive efficiencies and best practices for implementation processes, workflows, and tools Accountable for implementation client satisfaction scores and referenceable implementation clients Partner with Customer Strategy and Member Services teams to lead a smooth client transition from implementation to ongoing operations and account management Collaborate with the client lead from Customer Strategy to drive a smooth client transition from the sales cycle to implementation for the client and League teams About You: Minimum 10 years in healthcare management, delivery and/or consulting experience 10+ years of client management and/or program management required Prior engagement management and/or team management experience serving as the primary interface with senior client executive sponsors Proven track record of strong client management and customer service skills Strong leadership skills and a drive to make a large impact on the company and its clients Excellent written and oral presentation skills, with the ability to engage, inspire, build cr