Lead Product Manager, AI

🕒 May 26

🏄 California – Remote

🏄 California – Remote

⏰ Full Time

🟠 Senior

✅ Product Manager

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Sidecar Health

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2018

⚕️ Healthcare Insurance

Healthcare Insurance

Sidecar Health is a health insurance company that provides comprehensive major medical insurance with upfront pricing and no network restrictions or referral requirements. Their goal is to put employees in control of their healthcare by giving them a clear budget for care and allowing them to choose any doctor without surprise costs. They emphasize access to prescriptions without limitations and protection for unplanned care. Sidecar Health also offers transparent pricing and the option for members to save money if they find providers who charge less than their plan pays. Their offerings include individualized access plans and employer plans, ensuring members always have a choice of qualified doctors.

📋 Description

• Lead product strategy and execution for AI-powered member experiences • Define how and where AI capabilities should be applied across the member journey • Own product roadmaps for AI-driven features • Design human-in-the-loop workflows and fallback experiences • Define evaluation frameworks for AI product quality • Drive discovery and ideation for new AI-powered capabilities • Use data, experimentation, and user insights to measure AI feature performance • Partner with engineering and data science to scope AI initiatives • Lead a cross-functional pod of engineers, designers, and data scientists • Stay current on the rapidly evolving AI landscape

🎯 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 • Demonstrated experience taking AI products from concept through launch • Deep understanding of AI agents and agentic architectures • Strong instincts for designing trustworthy AI • Experience defining AI product quality metrics beyond traditional A/B testing • Founder or 0-to-1 builder experience is a strong plus • Proficiency in SQL for independent data analysis • Strong sense of design and UX, especially for AI-powered interfaces • Deep understanding of Agile methodology • Ability to communicate AI trade-offs, risks, and limitations to broad business audiences • 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.

🏖️ Benefits

• 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.