Lead Product Manager

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 Product Manager for claims automation at Sidecar Health, you will own critical claims platform features and systems that marry artificial intelligence and deterministic systems to power end to end claim processing, from the moment the data enters our system through claim finalization and payout.  You'll drive the strategy, development, and launch of AI-powered features — including agentic systems, intelligent assistants, and human-in-the-loop experiences — that ensure claims are processed quickly and correctly.

You bring a builder's mindset with a passion for automation and complex problems. You understand how to design for trust and auditability in non-deterministic systems and know when deterministic systems are the best approach.  You can think big in a systems view while diving into the details.  

What You'll Do 

• Own product strategy and roadmap for claims automation — spanning data extraction/entry, enrichment, identification, adjudication and routing across our claims processing platform  
• Become an expert on our operational processes and map them to technology and software solutions.  
• Define where AI/ML capabilities (document extraction, classification, sub-classification, routing) should be applied within the claims pipeline, and where logic should remain deterministic and rules-based  
• Define evaluation frameworks for AI product quality — accuracy, safety, hallucination risk, auditability, and user trust — and use them to make ship/no-ship decisions 
• Design human-in-the-loop workflows, audit trails, and escalation paths appropriate for a regulated, financial-transaction system  
• Define quality and turnaround-time (TAT) metrics for automated and semi-automated claims workflows, and use them to make ship/no-ship and rollout decisions  
• Drive build vs. buy decisions for claims infrastructure (e.g., pricing data, vendor tooling, etc) and make the call with clear tradeoff reasoning  
• Lead a cross-functional pod of engineers, designers, and data scientists to ship high-impact improvements 
• Lead complex, cross-functional initiatives — system migrations, platform upgrades, new payer/vendor integrations — from discovery through launch  
• Navigate compliance-driven requirements (e.g., No Surprises Act and other regulatory constraints) and translate them into clear, buildable product requirements  
• Partner closely with engineering, claims operations SMEs, and compliance stakeholders to scope initiatives, define MVPs, and sequence a heavily interdependent roadmap  
• Write clear, detailed PRDs and specs that hold up under scrutiny from engineering, compliance, and executive stakeholders  
• Use data and experimentation to measure the performance of automated workflows and continuously improve accuracy and throughput  
• Establish and evolve product practices suited to a platform that is part infrastructure, part intelligent system 
• 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 
• Set ambitious goals and hold yourself accountable 

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 working on processing systems with workflows, queues, routing, and automation.)  
• 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 
• Experience defining AI product quality metrics beyond traditional A/B testing 
• Strong instincts for designing auditable, traceable systems — this role sits inside financial-transaction and regulatory workflows where "mostly right" isn't sufficient without a clear audit trail  
• Strong sense of design and UX, especially for data dense applications and interactions 
• Demonstrated ability to write clear, rigorous specs for both deterministic systems (data pipelines, integrations, migrations) and non-deterministic ones (classification, extraction, routing logic), including how you evaluate and gain confidence in each 
• Experience partnering with engineering on build vs. buy vs. integrate decisions, including vendor evaluation  
• Proficiency in SQL for independent data analysis  
• Deep understanding of Agile methodology 
• Ability to manage a large number of interdependent workstreams and communicate sequencing tradeoffs to engineering, ops, and executive stakeholders  
• Experience working cross-functionally across engineering, operations, compliance, and business stakeholders  
• Claims processing, health insurance, or other regulated financial-transaction domain experience is a plus, but not required — we're equally interested in strong platform PMs from other complex domains 
• Startup 0-to-1 builder experience is a strong plus — we want people who've shipped under constraints and learned from real users 

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.