Senior QA Automation Engineer

Location Philadelphia, PA, or Remote (EST hours preferred) Overview Highlight Health is a mission-driven company that protects consumer rights and controls healthcare costs exclusively for self-funded employers and their stop loss carriers. We are a profitable, fast-growing company. We are currently upgrading our core operations into a sophisticated, proprietary Claims Intelligence Platform. This isn't a prototype; it is an innovative system of record handling protected health information (PHI) and generating financial recommendations with real-world legal and economic weight. Highlight Health engineers new ways to protect consumer rights and control healthcare costs for self-funded employers. Nearly every American has felt the pain of the skyrocketing cost of healthcare. Highlight Health brings them solutions. We use our subject-matter expertise to reduce costs for employers and relieve ordinary Americans of burdensome medical costs. Highlight Health is proud of its inclusive workplace that brings together highly skilled leadership and employees from all walks of life. We are looking for a Senior QA Automation Engineer to define and own our test practice from the ground up. Our engineering team builds in parallel using AI-assisted development as the default way of working, which means code ships fast; your job is to decide what “tested” means on this platform and build the coverage that proves it. At Highlight Health, the output of your work matters. You'll be defining test strategy for a platform where the “correctness bar” is exceptionally high, because the results directly affect what employers pay for healthcare and what our AI extraction pipeline reads from real claims documents. If you've built a QA practice from nothing before and want to do it again somewhere the stakes are real, we would love to hear from you. Essential Duties and Responsibilities Define and own the overall test strategy: the right mix of unit, integration, and end-to-end coverage, and where extraction-regression and data-isolation testing fit relative to UI testing. Define and own regression testing for our AI-assisted document extraction pipeline, validating structured output against a maintained set of known documents and expected results. Define and own row-level security and multi-tenant data isolation testing at the database layer, verifying isolation holds even when queries bypass the application layer. Define and own end-to-end browser test coverage for core workflows (case intake, review, packet generation, admin) using frameworks such as Playwright and Puppeteer scoped to packet/PDF output validation. Set testing standards for the engineering team to follow in their own feature work, and review test coverage on pull requests the way a senior engineer reviews code. Own synthetic test data generation, ensuring realistic edge-case coverage without ever using real, non-de-identified PHI. Bring test coverage and “definition of tested” decisions to compliance stakeholders for sign-off, rather than co-defining case by case. Serve as the team's primary point of judgment on testing and quality questions, escalating to the CTO only for decisions with broader business or release-timing impact. The Technical Stack End-to-end testing: Playwright (primary framework for browser-based workflow testing, cross-browser coverage, and AI-agent-driven test authoring via MCP). Document/PDF validation: Puppeteer (targeted use for packet generation output verification). Frontend unit/integration testing: Vitest, React Testing Library. Backend testing: pytest, with dedicated suites for extraction regression (golden-set) and row-level security. Database: Azure Database for PostgreSQL, row-level security enforced at both application and database layers. CI/CD: Azure DevOps pipelines. Compliance targets: HIPAA, SOC 2 Type 2. Experience and Qualifications 7-10 years in QA automation, including direct experience building a test practice from scratch at a company that didn't already have one, not just operating inside an established QA org. Demonstrated ownership of test strategy and tooling decisions, not just execution of someone else's plan. Hands-on production experience with Playwright or a comparable modern E2E framework; familiarity with Puppeteer a plus for document/PDF validation work. Strong SQL skills and comfortable with writing and reasoning about raw queries directly against PostgreSQL. Experience with modern frontend test frameworks (Vitest, Jest, or similar) and backend test frameworks (pytest or similar). Comfort designing tests for deterministic data-transformation problems, including AI/ML pipeline output validation and financial or structured data reconciliation. Hands-on experience using AI tools to generate, expand, or accelerate test coverage. Working knowledge of healthcare data compliance, or ability to ramp quickly with an internal compliance team. Comfortable being the senior voice on quality with no QA team above you. This role sets the standard, it doesn't inherit one. Healthcare or fintech background is a genuine advantage. This platform produces recommendations that affect what employers pay for healthcare. Compensation and Benefits Competitive salary based on experience. Highlight Health offers an attractive benefits package, including healthcare cost reimbursement, paid time off, commuting benefits, short-term disability, an employer 401(k) contribution, and bonuses. If you are based in the Philadelphia area, you will have the option of working in-office on a flexible schedule.