Lead Product Manager, AI

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.