Engineering Manager, AI Orchestration

Engineering Manager, AI Orchestration Location: Toronto, Ontario, Canada (remote eligible across Canada/US) Employment type: Full‑time About League Founded in 2014, League is a leading healthcare consumer experience platform powered by AI, serving over 63 million people worldwide. Payers, providers, and consumer health partners build on League’s platform to deliver high‑engagement healthcare solutions that improve health outcomes. With more than $285 million in venture capital funding, League powers digital experiences for trusted brands such as Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. The Role Lead a team of AI Engineers, software developers and data scientists responsible for building the “brain” of League’s AI platform—handling conversation state, tool execution, and the logic that turns raw model outputs into meaningful healthcare experiences. Beyond your direct reports, you will act as a delivery lead for the broader AI group, bringing structure, agile discipline, and operational excellence to ensure our Model Training research synchronizes seamlessly with Product Engineering delivery. In This Role You Will Team Leadership & Product Delivery: Manage and mentor a high‑performing AI team, own the AI Orchestration layer, translate architectural visions into actionable sprints, and conduct regular 1:1s. Agile Process & Cross‑Functional Coordination: Facilitate agile ceremonies across teams, coordinate dependencies with the AI Models team, and maintain internal processes that move work from research to production predictably. Architecture & Strategy: Collaborate with the VP of AI Architecture to define patterns for agent interaction with the League platform, leverage experience in stateful user applications for real‑time agent interaction, and identify headcount needs to build a diverse team capable of navigating the intersection of LLMs and Software Engineering. About You 5+ years of experience building and shipping software applications. Proven leadership experience with a track record of scaling teams and establishing an engineering culture. Strong process background—agile methodology across multiple stakeholders. Experience with state management and event‑driven architectures is a strong plus. Familiarity with LLMs and Agents is preferred, but a strong Software Engineering foundation is required. Security‑Related Responsibilities Compliance with Information Security Policies. Compliance with League’s secure coding practice. Ensure access management is performed in compliance with the employee’s role. Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations. Compensation (Canada only) $142,900—$214,300 CAD (base salary; excludes bonus, equity and benefits). Equal Employment Opportunity League committed to equal opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. If you need assistance during recruitment, contact Our Application Process Confirmation email after application submission. Recruiter reviews all applications. Recruiter reaches out if alignment exists and shares the interview process. Offer stage. Reference and background checks prior to joining; additional checks for US candidates. Work Location & Remote Policy Roles are office‑centric in Toronto or remote‑eligible. Toronto‑area Leaguers collaborate in‑office Monday‑Thursday, enjoy flexible remote days quarterly. Additional Resources Learn about our platform, leadership team and partners. Highmark Health, Google Cloud, League: new digital front door to seamless care. Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors. League raises $95 million USD in Series C to build world’s leading healthcare CX platform. Forbes x League: The Platformization Of Healthcare Is Here. Fast Company x League: If we want better innovations in healthtech, we need more competition. Use of AI Notice League may use AI tools to assist in screening applicants for this position. Privacy Policy Review our Privacy Policy for information on how League is protecting personal data. #J-18808-Ljbffr