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 perks 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!

📌 Sr Automation Engineer - US SaaS startup | Remote (Winnipeg)
🏢 Carrington Group of Companies
📍 Winnipeg