---
title: 'Lead Product Manager, Claims Automation at Sidecar Health'
canonical: 'https://feeny.ai/job/lead-product-manager-claims-automation-sidecar-health-remote-gekn6t8k2qvg'
type: 'job'
last_seen: '2026-10-15'
---

# Lead Product Manager, Claims Automation at Sidecar Health

- **Company:** Sidecar Health
- **Location:** Remote
- **Work type:** remote
- **Posted:** 2026-07-28
- **Last confirmed live:** 2026-10-15
- **Apply:** https://job-boards.greenhouse.io/sidecarhealth/jobs/6129263004

## Job description

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, This position is not eligible for visa sponsorship.*

## 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.

In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $200,000 - $220,000. 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.

## About Sidecar Health

## Company Overview
- **One-liner**: Sidecar Health is a health insurance company that provides ACA-compliant, employer-sponsored major medical plans with transparent pricing and no provider networks.
- **Entity Type**: Private (Series D)
- **Headquarters**: Manhattan Beach, California, USA
- **Founded**: 2018
- **Founders**: Patrick Quigley (CEO) and Veronica Osetinsky (COO)

## Core Business
- **Primary industry**: Health Insurance / Healthcare Technology
- **Target customers**: B2B — Large employers (fully insured and self-funded/ASO groups); previously served individuals
- **Mission**: To make quality healthcare affordable and accessible for all by bringing price transparency and consumer choice to health insurance

## Products & Services
- **Sidecar Health Employer Plans**: ACA-compliant major medical coverage for large employers. The model provides members with transparent, upfront pricing on care, allows them to shop for services, and shares savings when they choose lower-cost providers. Members keep 50% of the difference between the plan’s typical local cost and what they actually spend. The company covers members in 46 states and partners with employers across 50 industries. Plans are available as fully insured and administrative services only (ASO) for self-funded employers. [sidecarhealth.com](https://www.sidecarhealth.com/)

## Market Standing
- **Valuation**: Not publicly disclosed
- **Key Metric – Total Funding**: $328M (across 4 rounds)
- **Annual Revenue**: $50M (estimated, per LinkedIn data) [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Notable Investors**: Koch Disruptive Technologies (led Series D), Drive Capital (led Series C), Cathay Innovation (led Series B), GreatPoint Ventures, Morpheus Ventures [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Notable Advisors/Board Members**: Anne Wojcicki (CEO & Co-Founder, 23andMe), Andrew Liveris (President, Brisbane 2032 Olympic Committee), The Honorable David J. Shulkin, M.D. (Former Secretary of Veterans Affairs), Adam Stavisky (Former Walmart SVP, US Benefits) [sidecarhealth.com](https://www.sidecarhealth.com/about-us)
- **Growth Signals**: Headcount grew 18.7% YoY to 202 employees; active job postings surged 466.7% monthly and 1600% quarterly; expanded large group employer plans from Ohio to Georgia (2023) and Florida (2024); launched ASO capabilities for self-funded national employers in 2025. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Competitive Advantages
- **No provider networks**: Members can see any doctor or use any facility, removing the limitations of traditional narrow networks.
- **Transparent pricing engine**: The company shows guaranteed, local costs for care upfront, enabling members to shop and compare.
- **Shared savings model**: A behavioral economics approach that incentivizes members to be cost-conscious, which the company claims lowers overall costs for the entire group.
- **Carrier ownership**: Sidecar Health established its own insurance carrier (Sidecar Health Insurance Company) in 2021, allowing it to underwrite its own products and control the full insurance stack.
- **High claims approval rate**: The company reports approving over 99% of claims. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Strategic Focus
- **Shift to employer market**: After proving the model with individual plans, the company pivoted exclusively to employer-sponsored coverage, targeting large national employers.
- **Geographic expansion**: After launching in Ohio, the company expanded to Georgia and Florida, with a stated goal of covering members in 46 states.
- **Product breadth**: Offering both fully insured and ASO (self-funded) plans to capture different segments of the large employer market.
- **AI investment**: Actively hiring a Lead Product Manager, AI, signaling an investment in AI-powered capabilities. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)

## Why Work Here
- **Mission-driven work**: The company is explicitly focused on fixing a broken healthcare system, which attracts talent from tech, policy, and healthcare backgrounds.
- **Remote-first culture**: All current open positions (engineering, product, marketing, sales, member care) are listed as remote. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)
- **Strong ratings**: 4.2/5.0 on LinkedIn (117 reviews), with Culture rated 4.4 and Career rated 4.1. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)
- **Growth trajectory**: With a recent $165M Series D, rapid job posting growth, and a headcount expansion of nearly 19% YoY, the company is in a scaling phase — offering advancement opportunities.
- **Diverse team composition**: Team members come from backgrounds as tech leaders, policymakers, and healthcare professionals. The company is an Equal Opportunity employer. [job-boards.greenhouse.io](https://job-boards.greenhouse.io/sidecarhealth)
- **Open roles (as of mid-2026)**: 17 active job postings including Senior Software Engineer (Backend/Full Stack), VP of Marketing, VP of Strategic Accounts, Director of Account Management, Lead Product Manager (AI), and more. [linkedin.com](https://www.linkedin.com/company/sidecarhealth)

## Sources
1. [sidecarhealth.com - About Us](https://www.sidecarhealth.com/about-us)
2. [sidecarhealth.com - Homepage](https://www.sidecarhealth.com/)
3. [job-boards.greenhouse.io - Sidecar Health Careers](https://job-boards.greenhouse.io/sidecarhealth)
4. [linkedin.com - Sidecar Health Company Profile](https://www.linkedin.com/company/sidecarhealth)

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