Senior Software Development Engineer in Test

Sidecar Health is redefining health insurance with a mission to make healthcare affordable and accessible for everyone. They are seeking a Senior Software Development Engineer in Test (SDET) to join their Member Experience engineering team, focusing on building automation frameworks and ensuring quality across their health insurance platform. The role involves collaborating with product engineering teams to enhance quality engineering practices and implementing AI-powered testing solutions.

Responsibilities:

• 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

Requirements:

• 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