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Lead Product Manager, AI

May 29, 2026

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 <ul> <li class="font-claude-response-body whitespace-normal break-words pl-2">Lead product strategy and execution for AI-powered member experiences that help members find high-quality, cost-effective care</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Define how and where AI capabilities — LLMs, agentic workflows, conversational interfaces, intelligent recommendations — should be applied across the member journey</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Own product roadmaps for AI-driven features, balancing member needs, company goals, and technical feasibility</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Design human-in-the-loop workflows, fallback experiences, and guardrails that account for AI's probabilistic nature</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Define evaluation frameworks for AI product quality — accuracy, safety, hallucination risk, auditability, and user trust — and use them to make ship/no-ship decisions</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Drive discovery and ideation for new AI-powered capabilities that improve healthcare shopping, transparency, and personalization</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Use data, experimentation, and user insights to measure AI feature performance and iterate</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Partner with engineering and data science to scope AI initiatives, define MVPs, and navigate build vs. buy vs. integrate decisions</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Lead a cross-functional pod of engineers, designers, and data scientists to ship high-impact improvements</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Stay current on the rapidly evolving AI landscape and translate emerging capabilities into concrete product opportunities</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Establish strong product practices tailored to the unique challenges of shipping AI products</li> </ul> What You'll Bring <ul> <li class="font-claude-response-body whitespace-normal break-words pl-2">Bachelor's or Master's degree in Computer Science, Information Systems, Business Administration, or related field</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">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)</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Demonstrated experience taking AI products from concept through launch, including managing the unique challenges of non-deterministic systems — evaluation, safety, prompt design, user trust</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Deep understanding of AI agents and agentic architectures — you've shipped systems where AI takes sequences of actions, not just generates responses</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Strong instincts for designing trustworthy AI: traceable decisions, preserved intent, auditable outputs</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Experience defining AI product quality metrics beyond traditional A/B testing</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Founder or 0-to-1 builder experience is a strong plus — we want people who've shipped under constraints and learned from real users</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Proficiency in SQL for independent data analysis</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Strong sense of design and UX, especially for AI-powered interfaces where managing user expectations is critical</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Deep understanding of Agile methodology</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Ability to communicate AI trade-offs, risks, and limitations to broad business audiences without overpromising</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Experience working cross-functionally across engineering, data science, design, and business stakeholders</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Familiarity with AI safety, responsible AI practices, and healthcare-specific considerations is a plus</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Startup experience is a plus</li> </ul> What You'll Get <ul> <li>Competitive salary, bonus opportunity, and equity package </li> <li>Comprehensive Medical, Dental, and Vision benefits</li> <li>A 401k retirement plan</li> <li>Paid vacation and company holidays</li> <li>Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. </li> </ul><div class="content-conclusion">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.</div>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...