AI Automation Engineer

New York Cityfull timeRemote

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mid

$150k–$200k

H1B: no

Greenboard AI Automation Engineer at Greenboard to build and own the test framework, automated suites, and QA practices from scratch. Responsible for testing AI systems with non-deterministic output and ensuring data integrity at scale.

Responsibilities

You'll be our first dedicated Automation engineer. Our customers are regulated financial institutions, which means a missed bug is not just a bad user experience. It can mean an incomplete books-and-records archive, a marketing review that never routed for approval, or an attestation that quietly failed to send. Quality is part of the product we sell.
You'll own how we test: the framework, the automated suites, and the release process, built from scratch and then embedded with the engineers who ship. You'll also help us solve something most automation engineers have never had to solve, which is how to test AI systems whose output is not deterministic.
There is no existing playbook here. If you like defining the standard rather than enforcing someone else's, this is the seat.
The foundation. Test framework, automated regression suites, and QA practices built from zero, with your call on tooling
The critical paths. Message archiving and supervision, marketing review routing, employee attestations, and audit trails, which are the flows that cannot break
Testing the AI. How we evaluate AI-driven detection and review, including golden datasets and quality bars for output that is not deterministic
Data integrity at scale. End-to-end validation from ingestion of tens of millions of messages a day through to what a compliance officer sees on screen
The release gate. Bug triage, release sign-off, and the definition of deployment-ready at Greenboard
Love to move fast and build things
Looking for deep ownership over the quality of everything we ship
Obsess over the customers you're building for
An excellent communicator

Qualification

Have held a release beforeSat with a compliance officer

Required

3+ years testing software where being wrong has consequences beyond a bad review: fintech, healthtech, payments, or anywhere an audit followed a bug
Able to test a system you cannot fully see from the UI. Comfortable with REST APIs and querying the database directly, because verifying a feature here means checking what landed and what the retention policy did with it, not just what rendered
Write Playwright or Cypress suites that survive a redesign, with opinions about selectors, fixtures, and what belongs in an integration test versus an end-to-end one
Can read a feature spec and name the states nobody thought about: the employee who left mid-attestation, the message that arrives out of order, the marketing piece edited after approval
Have held a release before, explained why to someone who wanted it out, and been right

Preferred

Tested a system where output is not deterministic and had to define correct as a threshold rather than an exact match
Worked in a Node JS and React codebase on AWS, or debugged a queue-based ingestion pipeline
Been through a SOC 2 audit and know what evidence a test suite can produce for one
Sat with a compliance officer, an advisor, or a back-office team and watched them work
Interest in the financial industry is a plus, but not necessary