Company Overview:

The client is a venture-backed startup simplifying access to essential benefits for frontline workers. Their AI-powered platform helps employees easily find and apply for benefits like childcare, elder care, and nutrition programs.

With backing from major enterprise retail investors and $2.5M secured in funding, they're expanding their reach to serve leading retailers, healthcare providers, and Fortune 500 companies. Our diverse, remote-first team is spread across the globe, united in our mission to empower employees and create healthier workplaces.

They're currently on the brink of Series A funding, which means you'll have the opportunity to join them at an exciting stage of growth.

Your Role:

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.

You Bring:

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.

What They Offer:

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

This is an immediate hire, so apply today if you're ready to build the future of population care!