Lead Product Manager, AI

Responsibilities

• Lead product strategy and execution for AI-powered member experiences
• Define application of LLMs, agentic workflows, and conversational interfaces
• Own product roadmaps for AI-driven features
• Design human-in-the-loop workflows and guardrails for probabilistic AI
• Define evaluation frameworks for AI quality, including accuracy and safety
• Partner with engineering and data science to scope AI initiatives and MVPs
• Lead cross-functional pods of engineers, designers, and data scientists

Requirements

• 5+ years of product management experience
• 2+ years leading AI-powered product development (LLMs, agentic systems, or conversational AI)
• Experience managing non-deterministic systems (evaluation, safety, prompt design)
• Deep understanding of AI agents and agentic architectures
• Proficiency in SQL for independent data analysis
• Strong understanding of Agile methodology
• Must reside in California

Preferred Qualifications

• Founder or 0-to-1 builder experience
• Familiarity with AI safety and responsible AI practices
• Startup experience

About the Company

Sidecar Health is redefining health insurance with a mission to make excellent healthcare affordable and attainable for everyone through personalized and transparent systems.