Lead Product Manager, AI

Sidecar Health is redefining health insurance with a mission to make healthcare affordable and attainable for everyone. As a Lead AI Product Manager, you will own critical member-facing product areas where AI can transform healthcare access and decision-making, driving the strategy and development of AI-powered features.

Responsibilities:

• 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
• Stay current on the rapidly evolving AI landscape and translate emerging capabilities into concrete product opportunities
• Establish strong product practices tailored to the unique challenges of shipping AI products

Requirements:

• Bachelor's or Master's degree in Computer Science, Information Systems, Business Administration, or related field
• 5+ years of product management experience, with at least 2 years leading AI-powered product development (LLM-based features, agentic systems, conversational AI, or AI-assisted workflows — not solely traditional ML/predictive modeling)
• Demonstrated experience taking AI products from concept through launch, including managing the unique challenges of non-deterministic systems — evaluation, safety, prompt design, user trust
• Deep understanding of AI agents and agentic architectures — you've shipped systems where AI takes sequences of actions, not just generates responses
• Strong instincts for designing trustworthy AI: traceable decisions, preserved intent, auditable outputs
• Experience defining AI product quality metrics beyond traditional A/B testing
• Proficiency in SQL for independent data analysis
• Strong sense of design and UX, especially for AI-powered interfaces where managing user expectations is critical
• Deep understanding of Agile methodology
• Ability to communicate AI trade-offs, risks, and limitations to broad business audiences without overpromising
• Experience working cross-functionally across engineering, data science, design, and business stakeholders
• Founder or 0-to-1 builder experience is a strong plus — we want people who've shipped under constraints and learned from real users
• Familiarity with AI safety, responsible AI practices, and healthcare-specific considerations is a plus
• Startup experience is a plus