Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible 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!
The Opportunity
As Director of Claims Operations for Sidecar Health, you will own and scale the engine that delivers our core promise to members. This team is responsible for all member-facing and provider-facing claims operations, clinical programs, and claims automation strategy – powering a consumer-driven major medical insurance model that's redefining how Americans access and pay for care.
This is a high-stakes, high-opportunity role at an inflection point: we're expanding into new markets, deepening our AI-enabled automation stack, and building the claims infrastructure to support a rapidly growing membership base. You will lead a multidisciplinary team, shape the technology roadmap alongside Product and Engineering, and drive the operational excellence and compliance rigor that our members and the business depend on.
If you have a proven track record in health insurance claims leadership and a history of using AI and automation to transform operations — not just optimize them — we want to talk.
What You’ll Do
Build & Lead a High-Performance Claims Operation (50%)
- Lead and scale a multidisciplinary Claims Operations team — spanning claims adjudication, quality, operations, and clinical — to drive accurate, timely claims processing and an exceptional member experience
- Foster a culture of metrics-driven continuous improvement, accountability, and high performance across all Claims functions
- Develop future leaders within the team and build the bench for a growing, complex operation
Drive AI, Automation, and Operational Transformation (30%)
- Identify, prioritize, and lead automation that meaningfully increases end-to-end auto-adjudication rate, reduces claims processing time, and improves quality / accuracy
- Partner with Product and Engineering to shape the roadmap for claims technology —acting as a strategic voice, not just an operator
- Lead change management efforts as the team adopts new tools, workflows, and ways of working
- Build and maintain governance structures that support scalable, compliant, and data-informed operations
Own Claims Strategy & Business Outcomes (20%)
- Align claims operations with Sidecar Health's broader business objectives — including continued growth, sustainable MLR, and an obsessive focus on member experience
- Drive payment accuracy, fraud prevention, and claims spend optimization through proactive stakeholder management and cross-functional initiatives
- Translate operational data into strategic insights and recommendations for senior leadership
- Mitigate operational and regulatory risk while maintaining full compliance with healthcare regulations
- Own budget development and resource allocation, ensuring alignment with organizational priorities
What You’ll Bring
- 15+ years of operations experience, including 5+ years in healthcare
- 8+ years in senior leadership roles, leading large teams in complex environments
- Experience operating in a high-growth, tech-enabled health insurance or benefits company preferred
- Comfort with data — able to build and interpret operational dashboards and hold teams to metric-based goals
- Proven ability to lead through ambiguity, manage cross-functional stakeholders, and drive change in fast-moving environments
- Strong financial acumen — experience owning budget, headcount planning, and cost-per-claim targets
- Demonstrated results deploying AI or automation in a claims or complex operations environment
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
- 15+ years of operations experience
- 5+ years in healthcare
- 8+ years in senior leadership roles
- Experience in tech-enabled health insurance
- Ability to build and interpret operational dashboards
- Strong financial acumen
- Experience deploying AI or automation in operations
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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