Sr Automation Engineer

Role Description

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.

Qualifications

• 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).

Requirements

• 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.

Benefits

• Competitive salary (based on level and experience) + equity + PTO.
• Equity in a high-growth startup approaching Series A.
• Comprehensive benefits package (tailored to your location).
• The opportunity to make a tangible impact on people’s lives.
• A collaborative, remote-first culture.

Interview Process

• Screening: 45-minute chat with our Head of Product.
• Culture-fit interviews with 2-3 team members across different functions.
• 1-hour technical assessment (collaborative problem-solving).
• Final interview with founders and offer presentation.