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League

Principal, Software Delivery

Hybrid

Toronto, Canada

Senior

Full Time

26-01-2026

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Skills

Communication Leadership Change Management Sales Customer Service Presentation Skills Team Management Organization Project Management Organizational Skills 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 Principal, Implementation, 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 will

Manage, lead and oversee enterprise-level implementation with one of the company’s largest and most strategic customers Implement the project governance structure, including delivery structure, based on customer landscape
Facilitate and ensure adherence to change control, processes to support risk and issue escalation, decision making and program status
Collaborate on external communication plans and drive accountability for obtaining final approvals on client deliverables
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
Lead cross-functional internal and external teams (product, design, engineering, QA) to collaborate effectively on the creation of clear, actionable product requirements that align with project goals and meet customer needs
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
Develop and maintain strong relationships with external client counterparts; proactively identify opportunities to influence decisions and foster long-term partnerships that align with project goals
Maintain an understanding of League’s product and platform to inform key decisions during implementations
Lead internal teams and the client on a successful change management plan based on client pain points and objectives
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
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 credibility and engender trust across all levels of an organization.
Demonstrate resilience in managing customer relationships, handling challenges with professionalism and persistence while maintaining a positive, solutions-focused approach to meet customer needs
Strong business and technical acumen, and executive presence, combined with deep analytical and organizational skills
Results-oriented individual with a history of setting and attaining goals and meeting aggressive timelines
Confident, capable, enthusiastic self-starter with minimal need for direction
Experience at a SaaS, health-tech company, and/or start-up company highly preferred
Experience with project management software and tools

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 y

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