About League

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.

Position Summary

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 (Generalized Healthcare Intelligence: League's portfolio of healthcare-native SLMs), 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.

What You'll Do

• 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

What you bring:

• 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

AI Fluency & Ways of Working

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.

What this means in practice:

• 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 donefrom 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

How this scales by level:

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

What we look for:

• 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

Security-related Responsibilities

• 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

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.

Compensation range for Canada applicants only

$265,000—$315,000 CAD

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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.

Our Application Process:

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
• 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.

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Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here.

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