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. The Role As Principal, Implementation , you will be accountable for meeting customer deliverables as per contractual agreements (scope and time) and internal budget. You will drive disciplined execution through consistent methodologies, processes, and strong communication skills, ensuring the League product is implemented on time and with high quality to meet our clients’ business needs. Responsibilities 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. Build and maintain end‑to‑end integrated program plans, resource assignments, budgets and performance against targeted implementation milestones. 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 : Complete medical, dental and vision coverage. Bonus Program : Performance‑based bonus program. Employee Stock Option Program : Share in our success through a stock option program. Unlimited Paid Time Off : Recharge with unlimited PTO. Spending Accounts : Tax‑advantaged accounts for healthcare and dependent care expenses. Wellness Days : Dedicated wellness days throughout the year. Growth Opportunities : Professional development and advancement opportunities. Mentorship Program : Guidance from experienced leaders. Adaptable Ways of Working : Work in a way that suits your life and boosts productivity. Security‑Related Responsibilities Ensure access management is performed in compliance with the employee’s role and responsibilities. Responsibility and accountability for executing League’s policies and procedures within the department and team. Notification of HR, Legal, Compliance & Security of incidents, breaches or policy violations. Compliance with Information Security Policies. Compensation (Canada) Base salary range: $123,500 – $165,000 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 are an individual in need of assistance at any time during our recruitment process, please contact us at AI Notice League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here. Privacy Policy Review our Privacy Policy for information on how League is protecting personal data. #J-18808-Ljbffr

📌 Principal, Software Delivery - C$123,500 - C$165,000 A Year (Toronto)
🏢 League
📍 Toronto