Sidecar Health - Lead Product Manager, AI
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 • 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 • 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.
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
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