Engineering Manager, AI Orchestration

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 the Engineering Manager for AI Orchestration, you will lead the team responsible for building the "brain" of League’s AI platform. Your team builds the product layer that connects our users to our intelligence: handling conversation state, tool execution, and the logic that turns raw model outputs into meaningful healthcare experiences.

You are a pragmatic leader who understands that shipping AI products requires the discipline of software engineering combined with the flexibility of data science. You will manage a team of AI Engineers, software developers with a knack for AI, and data scientists with a passion for production code.

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 that our Model Training research synchronizes perfectly with our Product Engineering delivery

In this role, you will:

Team Leadership & Product Delivery

• Manage and mentor a high-performing team of AI Engineers, fostering a culture of rapid iteration and shipping value.
• Own the delivery of the AI Orchestration layer, including agent routing, conversation state management, and tool routing infrastructure.
• Translate complex architectural visions into actionable sprints and tasks; ensure the team is focused on high-impact work that drives League’s AI strategy.
• Conduct regular 1:1s, managing performance, career growth, and the unique cross-functional skill sets required for AI Engineering.

Agile Process & Cross-Functional Coordination

• Establish and facilitate agile ceremonies (stand-ups, planning, retrospectives) not just for your team, but to coordinate dependencies across the wider AI organization, specifically connecting AI infrastructure and model training workflows.
• Identify dependencies between the AI Models team (Data Science) and your team, ensuring that model capabilities are ready for integration when the application needs them.
• Create and maintain the internal processes for technical planning and documentation, ensuring we move from "research" to "production" predictably.

Architecture & Strategy

• Collaborate with the VP of AI Architecture to define the patterns for how agents interact with the League platform.
• Leverage your background in building complex, stateful user applications to solve challenges in real-time agent interaction and user session management.
• Identify headcount needs and drive recruiting 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 engineering culture.
• Strong process background: Demonstrated ability to implement agile methodologies and manage complex project lifecycles across multiple stakeholders.
• Experience with state management and event-driven architectures is a strong plus, as these concepts map directly to AI Agent orchestration.
• Familiarity with the AI landscape (LLMs, 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 and responsibilities
• Responsibility and accountability for executing League's policies and procedures within the department/ team
• Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

• You should receive a confirmation email after submitting your application.
• A recruiter (not a computer) reviews all applications at League.
• If we see alignment with League's needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
• The final step is an offer, which we hope you will accept!
• Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.

• 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

Work Location:

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.

Recognize and Avoid Employment scams. Practice safe job searching.