Lead Product Manager, AI

About the Role

As a Lead AI Product Manager at Sidecar Health, you will own critical member-facing product areas where AI can transform how people shop for and access healthcare. You'll drive the strategy, development, and launch of AI-powered features — including agentic systems, intelligent assistants, and LLM-powered experiences — that help members search for care, understand costs, and make more informed healthcare decisions.

You bring a builder's mindset. You've taken AI products from zero to one, you understand how to design for trust and auditability in non-deterministic systems, and you know that the hardest AI problems aren't technical — they're about decision integrity, user trust, and getting humans and AI to work together well.

What You'll Do

• Lead product strategy and execution for AI-powered member experiences that help members find high-quality, cost-effective care
• Define how and where AI capabilities — LLMs, agentic workflows, conversational interfaces, intelligent recommendations — should be applied across the member journey
• Own product roadmaps for AI-driven features, balancing member needs, company goals, and technical feasibility
• Design human-in-the-loop workflows, fallback experiences, and guardrails that account for AI's probabilistic nature
• Define evaluation frameworks for AI product quality — accuracy, safety, hallucination risk, auditability, and user trust — and use them to make ship/no-ship decisions
• Drive discovery and ideation for new AI-powered capabilities that improve healthcare shopping, transparency, and personalization
• Use data, experimentation, and user insights to measure AI feature performance and iterate
• Partner with engineering and data science to scope AI initiatives, define MVPs, and navigate build vs. buy vs. integrate decisions
• Lead a cross-functional pod of engineers, designers, and data scientists to ship high-impact improvements