Senior Automation Engineer

We are Skyward.
That is, a love for people, for improvement, for human advancement through information technology. We are a people-centered business with a desire to serve others. We are diverse and unified; creative and collaborative; a collection of complementary, not competing talents. And though on the surface we remain relaxed, beneath, a torrent of energy links us to our civic tech mission.
We stand by our values, and we won’t compromise on any of them.
Integrity: We’re conscientious, intentional, and empathetic. Our words and actions align. That’s our character. Please don’t ask us to play another part, we’re poor actors.   Compassionate: If we may borrow a quote from Theodore Roosevelt: “No one cares how much you know until they know how much you care.” Because our team is thoughtful and supportive, caring deeply for each other, our clients, and our work, this comes naturally. Inquisitive: We remain students by failing openly and turning lessons into solutions.Unconventional: For us, life isn’t what happens outside of work. Work happens inside of life and our culture erases the line often dividing the two.   Authentic: Made possible only because we embody the values listed above. We’re relaxed and fun yet intensely curious and driven. Team members are placed with thought, care, and precision to ensure that Trust, Truth, and Transparency continue to represent our brand.
Because of that, we continue Onward, Upward, and Skyward.
We need a Senior Automation Engineer.Are you the kind of person who can’t look at a machine learning model without wanting to test it six different ways (and then automate all six)? Do your friends sigh when you bring up responsible AI? Maybe they’ve stopped asking what you do for work because the last time you went on a 20-minute tangent about bias in training data and flaky CI pipelines for neural nets. If that sounds familiar, you might be exactly who we’re looking for.
Come join us if you're motivated to learn from others, to learn from mistakes, to be part of a future-looking and growth-oriented team.
Let's go Skyward together.

What you'll do:

• Be part of a team supporting the development of an AI/ML platform that will leverage generative AI to relieve user burden across the Centers for Medicare and Medicaid Services (CMS). 
• Design and maintain robust, scalable automated test frameworks for web apps, APIs, and AI-driven features.
• Develop automated pipelines for model validation, bias detection, and drift monitoring in ML-based systems.
• Define and execute test plans that include functional, regression, performance, and AI-specific testing strategies.
• Partner with AI/ML engineers to create test datasets and simulate real-world user behavior and edge cases.
• Implement CI/CD-integrated quality gates to ensure AI releases meet defined reliability and fairness metrics.
• Mentor junior engineers and help establish best practices in intelligent automation and AI testing.
• Advocate for ethical AI standards and contribute to cross-functional discussions about responsible AI.

What we'd like you to have:

• 5+ years of experience in software QA/automation engineering, with at least 2 years focused on AI/ML product testing.
• Strong proficiency in at least one automation framework (e.g., Selenium, Cypress, Playwright) and scripting language (Python preferred).
• Hands-on experience with testing AI models, including validation metrics, dataset versioning, and model explainability.
• Familiarity with tools like MLflow, TensorBoard, or similar for AI observability.
• Understanding of model bias, fairness audits, and compliance considerations in government or regulated environments.
• Experience working in Agile DevSecOps environments with modern CI/CD tooling (Jenkins, GitHub Actions, GitLab, etc.).
• Strong collaboration skills with a knack for clear communication across engineering, data science, and product teams.

What would blow us away:

• You’ve previously supported the Centers for Medicare and Medicaid Services (CMS).

Even if you don’t meet 100% of the qualifications, we encourage you to apply. At Skyward, we’re focused on hiring individuals with the right skills and passion to grow, not just checking off every box.

And now the important part. What we offer you:

• Medical, dental, vision insurance (fully paid for employees)
• 15 days of paid leave
• 7 days of sick leave
• 2 days bereavement leave
• 11 paid Federal holidays
• Up to 40 hours for jury duty
• 401K with 4% employer contribution (and no vesting period)
• Up to 4 weeks of paid paternity and maternity leave
• Company provided laptop
• $5,000 per year for professional development
• $600 per year for techni