VP, AI Platform Engineering

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.

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, the Data Platform leadership, and the AI Product leadership.

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 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.

• Use AI…