What we're trying to build

We want our test infrastructure to become an executable specification of the Dili compliance engine.

For each scenario, we should be able to define:

• the applicable regulation or program requirement, with citation
• the relevant project, payroll, worker, wage, and apprenticeship inputs
• the expected compliance determination
• the expected calculations, issues, remediation, and reporting behavior

These scenarios should be understandable by Compliance, version-controlled, automatically executable, and tied directly to release readiness.

Your first 90 days

First 30 days

• Learn the architecture of the compliance engine and how our engineering and Compliance teams currently validate changes
• Map at least one major compliance framework into a structured set of scenarios
• Identify the highest-risk gaps in our existing automated coverage

By 60 days

• Build the initial version of the compliance scenario registry
• Automate a meaningful set of high-priority scenarios, including regulatory citations and expected outcomes
• Establish a repeatable process for turning production defects into regression tests

By 90 days

• Have critical compliance scenarios running automatically in CI
• Give Engineering and Compliance clear visibility into coverage, failures, and known gaps
• Establish release-readiness criteria that provide concrete evidence that changes to the compliance engine are safe to ship

Must have

• Strong experience in software QA, quality engineering, or test automation
• Strong Python skills
• Experience building automated integration and end-to-end test suites
• Experience integrating testing into CI/CD and release processes
• Ability to test a Python/React application in an AWS environment
• Ability to systematically reason about complex combinations of rules, inputs, and expected outcomes
• Ability to turn written requirements into precise, deterministic test cases
• Strong attention to traceability: not just “did this test pass?”, but “why is this the expected behavior, and what requirement supports it?”
• Ability to work closely with engineers and domain experts to resolve ambiguity

Nice to have

• Recent hands-on experience with Playwright
• Experience with QA Wolf or similar modern QA tools
• Experience with parameterized, property-based, combinatorial, or model-based testing
• Experience testing payroll, tax, financial, legal, healthcare, insurance, or other rules-heavy software
• Experience with requirements traceability, release certification, or audit evidence

What success looks like

• Dili has a structured inventory of the compliance scenarios we support
• Critical scenarios are automatically tested and tied to authoritative regulatory sources
• Compliance can review and contribute to expected behavior
• Production defects become permanent regression tests
• Changes to regulations or interpretations can be traced to affected scenarios
• Releases provide clear evidence of what was tested and whether the compliance engine is ready to ship

A meeting lands on your calendar

If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.