--- title: 'Staff Software Engineer, Full Stack (Member Benefits) at Sidecar Health' canonical: 'https://feeny.ai/job/staff-software-engineer-full-stack-member-benefits-sidecar-health-remote-jed2cz2vjnqa' type: 'job' last_seen: '2026-10-15' --- # Staff Software Engineer, Full Stack (Member Benefits) at Sidecar Health - **Company:** Sidecar Health - **Location:** Remote - **Work type:** remote - **Posted:** 2026-09-22 - **Last confirmed live:** 2026-10-15 - **Apply:** https://job-boards.greenhouse.io/sidecarhealth/jobs/6205660004 ## Job description 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! ## About the Role Healthcare runs on data moving between systems that were never designed to talk to each other. Provider directories, benefit and pricing feeds, claims data, and a long tail of third-party partners each with their own format and quirks. You'll own the platform that makes that data usable: the pipelines that land it in Snowflake, the delivery pipelines that gets it back out to partners, and the third-party integrations that keep it flowing correctly at scale. You'll also build the internal tools that let our operations and pricing teams move fast without waiting on engineering for every change. Things like automating pricing adjustments for benefit amounts across large provider datasets, so repetitive manual work becomes a self-serve, auditable workflow. This is a Staff-level role. You'll be expected to set technical direction for how we handle data at scale, unblock other engineers who are heads-down on features, and be the person the team turns to when a data pipeline or integration problem doesn't have an obvious answer. **MUST BE BASED IN CALIFORNIA, OREGON OR WASHINGTON, This role is not eligible for sponsorship** ## What You'll Do - Own and evolve the production services and APIs that power provider, benefit, and pricing experiences for members, partners, and internal teams, including the data flows into Snowflake and out to third-party consumers - Design, build, and operate third-party integrations as resilient production services (idempotent, retry-safe, and observable), handling schema drift, malformed data, and partner-specific quirks gracefully - Build full-stack internal products that automate repetitive, high-volume operational work (e.g., pricing adjustments for benefit amounts) — turning manual processes into scalable, self-service applications with clear UX and audit trails - Ensure the production services handling large volumes of medical provider data meet a high bar for correctness, latency, data quality, and auditability - Set technical direction for service architecture and integration patterns — evaluate and introduce modern architectural approaches (service-oriented design, API contracts, event-driven systems, workflow orchestration, etc.) where they solve real problems - Act as a technical unblocker across teams: review designs, pair on hard problems, and help other engineers ship product features rather than stall - Drive engineering standards for production reliability: SLOs, observability, alerting, testing, and safe deployment practices (feature flags, canary releases, fast rollbacks) - Take part in and help shape on-call and incident response: lead root-cause analysis and drive the fixes that prevent repeat incidents - Partner closely with product, operations, and pricing stakeholders to translate ambiguous business needs (like "automate this pricing process") into durable product capabilities and production services - Mentor engineers and raise the technical bar through code review, design docs, and hands-on collaboration ## What You'll Bring - 10+ years of professional software engineering experience, with a track record of owning data-intensive systems in production - Deep experience building and operating data pipelines at scale; ingestion, transformation, and delivery (Snowflake experience strongly preferred) - Hands-on experience building and maintaining third-party integrations, including handling unreliable or inconsistent external data - Experience building internal tools/platforms that automate operational workflows for non-engineering teams - Strong fundamentals in distributed systems, data modeling, and modern architectural patterns for processing data at scale - Demonstrated ability to operate as a technical leader: setting direction, unblocking others, and influencing without direct authority - Comfort with ambiguity; you can take a loosely defined operational pain point and turn it into a well-scoped technical solution - Strong communication skills; able to explain a data architecture tradeoff to both engineers and non-technical stakeholders - Fluent, disciplined use of AI-assisted tooling to move faster, with the rigor to verify correctness, security, and quality before it ships Nice to haves: - Experience with healthcare data (provider directories, NPI, claims, fee schedules, or benefits data) - Familiarity with workflow orchestration tools (Airflow, dbt, Step Functions, etc.) The Reality This is a startup. We move fast. We prioritize impact over polish. We expect: - Bias for action — ship, learn, iterate - Ownership — you design it, build it, run it - Pragmatism — solve real problems, not theoretical ones - Resilience — ambiguity comes with the territory Healthcare is complex and broken. The work matters. ## 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 - $240,000. 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) ## Other roles at Sidecar Health - [Staff Data Analytics Engineer](https://feeny.ai/job/staff-data-analytics-engineer-sidecar-health-remote-ty366nskbbn3) - [Marketing & Events Coordinator, Broker & Partnerships](https://feeny.ai/job/marketing-events-coordinator-broker-partnerships-sidecar-health-remote-9rz8gfd8vprx) - [Lead Product Manager, Claims Automation](https://feeny.ai/job/lead-product-manager-claims-automation-sidecar-health-remote-gekn6t8k2qvg) - [Account Manager, Client Services - Texas](https://feeny.ai/job/account-manager-client-services-texas-sidecar-health-remote-r1t3ch8hevm7) - [VP of Strategic Accounts](https://feeny.ai/job/vp-of-strategic-accounts-sidecar-health-remote-dx7xv2b9sj0n) - [VP of Finance](https://feeny.ai/job/vp-of-finance-sidecar-health-remote-svc5b8sd95fr)