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.
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.
Skills Required
- 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
- Experience taking AI products from concept through launch, including non-deterministic system challenges
- Deep understanding of AI agents and agentic architectures
- Experience defining AI product quality metrics beyond traditional A/B testing
- Strong instincts for designing auditable, traceable systems for regulated financial-transaction workflows
- Strong sense of design and UX for data-dense applications and interactions
- Ability to write clear, rigorous specs for deterministic and non-deterministic systems
- 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 many interdependent workstreams and communicate sequencing tradeoffs
- Experience working cross-functionally across engineering, operations, compliance, and business stakeholders
- Claims processing, health insurance, or other regulated financial-transaction domain experience
- Startup 0-to-1 builder experience
Sidecar Health Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Sidecar Health and has not been reviewed or approved by Sidecar Health.
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Fair & Transparent Compensation — Compensation in tech and product roles is described as market‑aligned and competitive. Feedback suggests many in these functions feel total pay stacks up well against peers.
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Healthcare Strength — Employer‑paid major‑medical coverage for employees and family is highlighted, positioning health benefits as a strong component of total rewards. Feedback suggests low denial rates, added navigation tools, and center‑of‑excellence partnerships reinforce the plan’s practical value.
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Equity Value & Accessibility — Total rewards are presented to include stock options and bonuses in addition to salary. Feedback suggests these elements can meaningfully enhance perceived upside beyond base pay.
Sidecar Health Insights
What We Do
Sidecar Health is changing the health industry with modern, common-sense health insurance that finally gives consumers control over costs and choices. We are a passionate group of people-people on a mission to make quality healthcare affordable and accessible for everyone.
Why Work With Us
Being a growth-stage distributed startup, transparent and asynchronous communication is critical. We'll provide you with the resources and tools you need, and regularly seek your feedback through quarterly engagement pulses on what is or isn't working well.
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