Principal, Delivery

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.

• 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

• 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.
• 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
• Bachelor’s degree or equivalent years of experience

• →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 any incidents, breaches or policy violations
• →Compliance with Information Security Policies

• →Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• →Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• →Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• →Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively
• →Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information

• →Individual Contributors: Use AI to improve personal productivity and quality of output
• →Senior ICs / Managers: Integrate AI into team workflows and improve processes
• →Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

• →Demonstrated experience using AI tools in a practical, responsible way
• →Curiosity and openness to experimenting with new technologies
• →Ability to balance efficiency with quality and sound judgment

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in-office Monday through Thursday. Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.