VP, AI Platform Engineering - Remote Eligible

VP, AI Platform Engineering

League is building the agentic platform for healthcare: the harness, orchestration, and runtime that turn frontier and healthcare-native models into deployed intelligence inside member-facing care experiences. This is the layer that sits between the models and the member; the one that decides what an agent can do, what it can't, how it composes with other agents, and how its work shows up in the product. We're looking for a VP, AI Platform Engineering to lead the team that builds it. This role leads engineering for League's agentic platform — the multi-agent orchestration runtime, agent harness, evaluation and guardrail infrastructure, and the developer surface that other teams at League use to ship domain agents into production. It is a peer to the AI Models leadership that owns the intelligence layer that the Data Platform leadership that owns the data substrate, and the AI Product leadership that owns the consumer-grade agentic experience. Together these functions form the Data & AI First Team that owns League's bet on healthcare AI end-to-end.

The agentic platform: You own the engineering of League's multi-agent orchestration runtime; the harness, framework, model-routing layer, and evaluation and guardrail infrastructure that runs every agent League ships. The platform is the layer between the models and the member; how good it is determines how much intelligence League can actually deploy

The developer surface: You own the engineering of the platform that League's teams and League's customers use to build, simulate, configure, and evaluate agents; the SDK, tooling, simulation environment, and configuration surfaces that turn the agentic harness into a product the rest of League and the market build on. Success is measured by how much agent functionality ships across League and across League's customers without going through your team

The team: You lead the engineers and managers who build the agentic platform. Building the bench is part of the work: this org will grow with the platform, and your hiring bar will set the ceiling for what we ship

The First Team: You sit on League's Data & AI leadership team alongside the leaders of AI Models, Data Platform, and AI Product, where the bets that decide League's healthcare AI strategy get made. The work runs both ways: shaping cross-cutting decisions on model strategy, evaluation methodology, and data contracts inside League, and carrying technical credibility into the conversations with customers and partners

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

At League, we are an AI-native organization. We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

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

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

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

Compliance with Information Security Policies

Compensation range for Canada applicants only

$265,000 - $315,000 CAD

Our employees come from different backgrounds, and we celebrate those differences. 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 .

Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let's do ours by sharing potential next steps

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.

Here are some additional resources to learn more about League:

Learn about our platform, leadership team and partners

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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

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.

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