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About the Role

League is building the agentic platform for healthcare, serving as the harness, orchestration, and runtime for AI models within member-facing care experiences. We are seeking a VP, AI Platform Engineering to lead the team responsible for building this platform, which includes multi-agent orchestration, agent harness, evaluation and guardrail infrastructure, and developer surfaces. This role is a key part of the Data & AI First Team, collaborating with AI Models, Data Platform, and AI Product leadership to shape League's healthcare AI strategy.

Responsibilities

Own the engineering of League's multi-agent orchestration runtime, including harness, framework, model-routing layer, and evaluation/guardrail infrastructure.
Own the engineering of the platform used by League teams and customers to build, simulate, configure, and evaluate agents (SDK, tooling, simulation environment, configuration surfaces).
Lead the engineers and managers building the agentic platform and focus on building the team's bench strength.
Shape cross-cutting decisions on model strategy, evaluation methodology, and data contracts as part of the Data & AI leadership team.
Carry technical credibility into customer and partner conversations.
Ensure access management is performed in compliance with the employee's role and responsibilities.
Take responsibility and accountability for executing League's policies and procedures within the department/team.
Notify HR, Legal, Compliance & Security of any incidents, breaches or policy violations.
Comply with Information Security Policies.

Requirements

Proven experience building and operating AI systems in production at enterprise scale.
Experience leading platform engineering teams that enable multiple product and engineering organizations.
Strong track record building high-performing engineering cultures and developing senior technical talent.
Deep understanding of AI platform architecture, infrastructure, scalability, reliability, and operational excellence.
Pragmatic operator mindset with a focus on solving high-impact problems and shipping customer-ready solutions.
Strong technical judgment with the ability to balance innovation, speed, and business value.
Experience partnering cross-functionally across Product, Data, Infrastructure, Security, and Go-to-Market teams.
Excellent communication and executive presence, with the ability to influence technical, customer, and executive audiences.
Strong understanding of the modern AI ecosystem, including emerging platform, tooling, and deployment patterns.
Track record of delivering measurable business and operational impact through AI and platform engineering initiatives.
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.
Do not expect applicants to meet every qualification to be considered.

Skills

AI Platform Engineering
Multi-agent orchestration
Agent harness
Evaluation and guardrail infrastructure
Developer surfaces
SDK
Tooling
Simulation environment
Configuration surfaces
AI systems
Platform engineering
AI platform architecture
Scalability
Reliability
Operational excellence
AI ecosystem
AI tools

Location

Toronto
Canada
US

Work Type

Office-centric
Remote-eligible
Full-time

Experience Level

Salary/Compensations

$265,000—$315,000 CAD

About the Company

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.
At League, we are an AI-native organization.
We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.

Equal 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 recruitinginfo@league.com.