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.
Skills Required
- Bachelor's or Master's degree in Computer Science, Information Systems, Business Administration, or related field
- 5+ years of product management experience
- At least 2 years leading AI-powered product development
- Demonstrated experience taking AI products from concept through launch
- Proficiency in SQL for independent data analysis
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
-
Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
-
Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
-
Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
Sidecar Health Insights
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
Gallery
