About the role

Automation Engineer responsible for creating reliable automation for web portals. Join a US startup revolutionizing benefits for frontline workers with AI, working remotely.

Responsibilities

You’ll build and maintain reliable automation that interacts with real-world web portals and third-party systems—where correctness, traceability, and security matter as much as speed
Own the design, development, and operation of web-portal automation workflows using Playwright (and related tooling)
Build automation services primarily in Python , with strong supporting development in TypeScript
Implement evaluation/validation (“evals”) to measure automation accuracy, catch regressions, and improve reliability over time
Maintain strong audit-trail discipline : deterministic logging, event traces, artifacts, and reproducible runs for debugging and compliance needs
Design automation with a security-first mindset , following best practices for handling sensitive workflows and data
Collaborate with engineering/product stakeholders to translate ambiguous real-world processes into pragmatic, shippable automation
Improve robustness against common automation challenges (dynamic UIs, flaky states, rate limits, auth flows, partial failures) while keeping systems maintainable

Strong experience building production-grade systems in Python and TypeScript
Hands-on experience with Playwright or similar browser automation frameworks (Selenium/Puppeteer), ideally for portal automation at scale
A “pragmatic shipper” mindset: you prioritize delivering reliable working software over research-heavy approaches
Comfort building systems with strong observability: structured logs, metrics, alerts, and clear debugging workflows
Experience creating or maintaining automated testing/evals , quality gates, and release discipline
Solid understanding of secure engineering practices (secrets management, least privilege, secure auth patterns, safe handling of sensitive data)
Bonus points: Experience working in compliance-heavy environments (e.g., HIPAA , SOC 2)
Experience designing audit-ready systems (traceability, change management, access logging)
Experience automating complex multi-step workflows across multiple vendor portals with inconsistent UX
Experience hardening automation against adversarial or brittle UI behavior (captcha-like flows, frequent UI changes, bot detection constraints) in legitimate/compliant ways