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
We're looking for a Senior SDET to join our Member Experience engineering team and own the quality engineering foundation for the products our members interact with every day—from finding care and understanding benefits to submitting claims and managing their health plans.
This is a hands-on, high-impact individual contributor role. You won't be managing a team—you'll be the person who builds the automation frameworks, designs the regression suites, and ensures we catch issues before our members ever see them. You'll work closely with our Director of Engineering for Member Experience and embed directly with product engineering squads to shift quality left across the entire development lifecycle.
We're also building toward an AI-powered approach to quality engineering. You'll help us explore and implement AI-assisted testing—from intelligent test generation and self-healing test suites to building QA agents that can autonomously validate complex member workflows. If you're excited about the intersection of test automation and AI, this is the role.
**MUST BE BASED IN CALIFORNIA**
What You'll Do
- Design, build, and maintain scalable test automation frameworks across our member-facing applications (web and mobile), covering UI, API, and integration layers
- Develop and own a comprehensive regression suite that provides confidence for every release across our multi-state health insurance platform
- Embed with product engineering teams to shift quality left—writing testable acceptance criteria, designing test strategies during sprint planning, and catching defects early in the development cycle
- Build and maintain CI/CD-integrated test pipelines that provide fast, reliable feedback on every pull request and deployment
- Pioneer AI-powered quality engineering: explore and implement LLM-assisted test generation, intelligent test maintenance, and autonomous QA agents that can validate complex claims, benefits, and member workflows
- Investigate and triage production issues, perform root cause analysis, and build targeted regression tests to prevent recurrence
- Define quality metrics and reporting that give engineering leadership visibility into test coverage, defect trends, and release readiness
- Champion a quality-first culture across the Member Experience engineering organization—mentoring and showcasing testability best practices to developers
What You'll Bring
- Significant hands-on experience as an SDET, Test Automation Engineer, or Quality Engineer in a software product environment
- Deep expertise building test automation frameworks from scratch (not just writing scripts in existing frameworks)—you've made architectural decisions about tooling, patterns, and infrastructure
- Strong programming skills in Java, Python, TypeScript, or similar languages; you write production-quality code
- Experience testing modern web applications built on frameworks like React/Next.js/React Native/Flutter and backend services on Spring Boot or similar JVM-based stacks
- Proficiency with API and integration testing tools and practices (REST, GraphQL, contract testing)
- Hands-on experience integrating automated tests into CI/CD pipelines (GitHub Actions, Jenkins, or similar)
- Experience with cloud infrastructure (AWS preferred): understanding of how to test applications running on Lambda, Step Functions, API Gateway, DynamoDB, and related services
- Strong debugging and root cause analysis skills—you can read application code, trace through distributed systems, and pinpoint where things break
- Excellent communication skills and the ability to influence engineering teams on quality practices as a peer, not a gatekeeper
- Bachelor's degree in Computer Science or equivalent practical experience
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.
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
- Experience as an SDET, Test Automation Engineer, or Quality Engineer
- Experience building test automation frameworks from scratch
- Strong programming skills in Java, Python, or TypeScript
- Experience testing web applications built on modern frameworks
- Experience with API and integration testing practices
- Hands-on experience integrating automated tests into CI/CD
- Experience with cloud infrastructure, preferably AWS
- Strong debugging and root cause analysis skills
- Excellent communication skills
- Bachelor's degree in Computer Science or equivalent
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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