Principal, Software Delivery

Join to apply for the Principal, Software Delivery role at League About League Founded in 2014, League is a healthcare consumer experience (CX) platform powered by artificial intelligence (AI), reaching more than 63 million people worldwide and delivering high levels of personalization. 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 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 consistent methodologies, processes, and strong communication. You will be a passionate advocate for the League product and ensure the platform is implemented on time and with high quality to meet 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 the 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 end-to-end integrated program plans, resource assignments, budgets and performance against milestones for the implementation 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 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 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 sales 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 with 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 Demonstrated resilience in managing customer relationships with professionalism and persistence while maintaining a solutions-focused approach Strong business and technical acumen, executive presence, and deep analytical and organizational skills Results-oriented with a history of achieving goals and meeting aggressive timelines Confident, motivated self-starter with minimal need for direction Experience at a SaaS, health-tech company, and/or startup is highly preferred Experience with project management software and tools What We Offer Comprehensive Health Benefits: medical, dental, and vision coverage Bonus Program: performance-based bonus Employee Stock Option Program: stock options Unlimited Paid Time Off and flexible working options Spending Accounts for healthcare and dependent care Wellness Days throughout the year Growth Opportunities and Mentorship Flexible Ways of Working Security-related Responsibilities Ensure access management is performed in alignment with roles and responsibilities Policy and procedure compliance within the department Notify HR, Legal, Compliance & Security of incidents or policy violations Compliance with Information Security Policies Canada applicants only: The compensation range below is specific to this role in Canada and excludes bonus, equity and benefits. Salary ranges reflect base salaries across Canadian locations and may vary by skills and experience. More details provided by your recruiter during the process.Compensation range for Canada applicants only: CA$123,500—CA$165,000 Our employees come from diverse backgrounds. We are committed to equal employment opportunity and encourage applications from all qualified individuals. If you need assistance during the recruitment process, please contact Our Application Process You will receive a confirmation email after applying. A recruiter reviews applications to determine fit. If aligned, a recruiter will reach out to discuss goals and team interview processes. The final step is an offer, subject to reference and background checks where applicable. Work Location We have a mix of office-centric roles in Toronto and remote-eligible roles in Canada or the US. Location details will be indicated in each posting. Toronto-area Leaguers may be in-office Monday–Thursday. Flexible remote days are available based on distance to the office. #J-18808-Ljbffr