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Greenboard is building an AI-native compliance operating system for regulated financial institutions including RIAs, fintechs, private funds, and hedge funds. The platform replaces fragmented legacy tools and automates compliance workflows at scale, helping firms reduce regulatory risk and modernize operations. Backed by Y Combinator and General Catalyst with $20M+ raised, the company is growing rapidly with brand-name financial institutions as customers.
You will be Greenboard's first dedicated Automation Engineer, owning the quality and testing strategy from the ground up. This is a high-stakes role: bugs don't just create poor user experiences—they can result in incomplete compliance archives, failed approval routing, or missed attestations with regulatory consequences.
Key responsibilities include:
- Building the test framework, automated regression suites, and QA practices from scratch, with full ownership of tooling decisions
- Owning critical compliance workflows (message archiving, supervision, marketing review routing, employee attestations, audit trails) that cannot fail
- Solving a novel problem: testing AI systems with non-deterministic output, including defining golden datasets and quality thresholds
- Ensuring data integrity at scale across tens of millions of daily messages from ingestion through compliance officer dashboards
- Serving as the release gate: bug triage, release sign-off, and defining deployment readiness standards
The founding team includes engineers from Amazon, Google, and multiple unicorn startups. You'll work closely with product and engineering to embed quality practices across the organization and define standards rather than enforce existing ones.
REQUIREMENTS:
- 3+ years testing software in high-consequence domains (fintech, healthtech, payments, or similar where audit failures follow bugs)
- Ability to test systems beyond the UI: comfortable with REST APIs and direct database queries to verify data flow and retention
- Proficiency writing Playwright or Cypress suites that survive redesigns, with strong opinions on selectors, fixtures, and test scope (integration vs. end-to-end)
- Ability to identify edge cases and untested states from feature specs (e.g., mid-process user departure, out-of-order messages, post-approval edits)
- Experience holding releases, explaining delays to stakeholders, and being proven correct
NICE TO HAVE:
- Experience testing non-deterministic systems and defining correctness as a threshold
- Familiarity with Node.js and React codebases on AWS, or queue-based ingestion pipeline debugging
- SOC 2 audit experience and understanding of test evidence requirements
- Exposure to compliance workflows through direct observation of compliance officers or back-office teams
- Interest in financial services (not required)
