Lead Product Manager, AI

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen. The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent. If you want to use your talents to transform healthcare in the United States, come join us! **Must reside in California for consideration** 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 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 What You'll Bring 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 Founder or 0-to-1 builder experience is a strong plus — we want people who've shipped under constraints and learned from real users 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 Familiarity with AI safety, responsible AI practices, and healthcare-specific considerations is a plus Startup experience is a plus What You'll Get Competitive salary, bonus opportunity, and equity package Comprehensive Medical, Dental, and Vision benefits A 401k retirement plan Paid vacation and company holidays Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.