[Hiring] Lead Product Manager, Claims Automation @Sidecar Health

Role Description

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.

Qualifications

• 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.

Benefits

• 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.

Company Description

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.