Lead Product Manager, Claims Automation

Sidecar Health is redefining health insurance with a mission to make excellent healthcare affordable and attainable for everyone. As a Lead Product Manager for claims automation, you will own critical claims platform features and systems that integrate artificial intelligence to enhance claim processing efficiency and accuracy.

Responsibilities:

• 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

Requirements:

• 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