About this role
The stack: Node.js/Express, TypeScript, React, Postgres, Clickhouse, MongoDB, Heroku
The product: We're building agentic software for Finance and Operations teams to automate high-volume workflows across systems—from AP and AR to payroll, inventory, and reconciliations. See www.woodrow.ai
The way we work:
This is a remote job—work anywhere you want, in any timezone on earth (or outside it). We are an asynchronous team—no scheduled meetings. We rely on each team member to pick their own schedule and communicate clearly in writing and recorded videos. We operate completely autonomously—no one will tell you what to do, we'll tell you the goals and you'll figure out how to work towards them with the rest of the team.
The role:
We're looking for our first Quality & Reliability Engineer who thinks about quality as a system, not a phase at the end of development.
You'll own quality and reliability across the stack—from test infrastructure to production monitoring to LLM evals. This is a founding role: you'll assess what we need, prioritize ruthlessly, and build the foundations that let us ship fast without breaking things.
This is not a traditional QA role. You may review some pull requests and help write e2e tests, but you will ALSO own the monitoring side and build guardrails that scale—all with the goal of preventing and catching issues before customers do.
This role combines elements of software engineering, traditional QA, reliability engineering, and devops.
What you'll work on:
CI & Test Health
Make sure tests consistently run fast and green means greenMaintain staging and test environments that are usefulHelp review code with a focus on reliability, edge cases, and failure handlingBuild and maintain integration and end-to-end test suitesClose gaps in test coverage by writing tests yourself AI Quality & Evals
Monitor AI workflow correctness and audit individual workflows to catch regressionsDesign and maintain eval suites for LLM featuresBuild a repeatable process for validating prompt changes before they shipObservability & Production Health
Design and implement monitoring, alerting, and dashboards so we understand system health at a glanceOwn observability for our data pipelines external integrations, and AI workflowsMake sure we know about failures before customers tell us Requirements
You're an excellent engineer—you can solve hard problems, you're AI Native, and ship quicklyExperience with observability tooling (Datadog, Sentry, or similar)Strong testing background (unit, integration, e2e; automation frameworks) both writing, as well as architectingFamiliarity with LLM-based features and eval approaches (or willingness to learn quickly)Great communicator via writing and recorded videoComfortable working in ambiguous, fast-changing environmentsExcited about working on a globally-distributed, diverse team where autonomy, accountability, and ownership matter as much as your skillsetBenefits
Unlimited vacationCompletely flexible work schedule—work literally anytime (and anywhere) you wantBenefits appropriate to your location (health/dental/vision in the USA)Company-wide retreats multiple times per yearMarket-rate compensation including benefits—we're scrappy, but not scrappy on compensation