Lead Product Manager, Sidecar Health
A.I.
+ Equity + Bonus
Digital health insurance platform
Be an early applicant
Digital health insurance platform
201-500 employees
Be an early applicant
+ Equity + Bonus
201-500 employees
Company mission
To make healthcare affordable.
Role
Who you are
- 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 the job involves
- 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
- 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
Our take
Sidecar Health’s insurtech platform allows users to tailor their own flexible healthcare plans based on their individual needs and budget. One of its main advantages outside of its flexibility is how the company doesn't use its own dedicated network of doctors, allowing the customer to see whomever they like while negating its own need to build nationwide networks.
Furthermore, it allows users to search and compare local health providers, and pay directly for care through its own payment card, often at a discount to what legacy insurance providers charge. Sidecar’s offering allows for better flexibility, more transparency and fewer financial burdens for unnecessary coverage areas.
The company has garnered plenty of praise and financial backing for its consumer-centric approach. Its 2024 funding raise positions Sidecar Health as a major disruptor in the market. That said, future growth will depend on how well it can expand its nationwide footprint, take on the legacy healthcare providers and work its way into employer and government-sponsored plans. 2026 expansions into the state of Texas show it is making progress on these fronts.
Steph
Company Specialist at Welcome to the Jungle
Insights
-28% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Jun 2024
$165m
SERIES D
Jan 2021
$125m
SERIES C
Total funding: $328m
Company benefits
- Comprehensive Medical, Dental, and Vision benefits
- Paid vacation and company holidays
- Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S
Company HQ
Manhattan Beach, CA
Leadership
Patrick Quigley
(Co-Founder & CEO)Having worked at BEA Systems and QuinnStreet for a combined 8 years, they took an MBA at Wharton. They also served as CEO of Healthplans.com and Katch.
Veronica Osetinsky
(Co-Founder & COO)They studied at UCB before working at Bank of America and Paramax Capital. They worked at Quinstreet and Katch for 8 years prior to co-founding Sidecar Health.
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