Checkly Support Engineer at Checkly supports customers by debugging Playwright tests, analyzing API check failures, and improving AI support processes. This remote role involves working with modern tooling and contributing to product improvements.
Responsibilities
Support has always been about solving real problems for real people. What’s changing at Checkly is how we do it: AI lets us automate routine work and assist us with troubleshooting, so we can go deeper on hard cases and bring what customers tell us straight back to the product. Here’s where you come in:
Resolve customer issues. Debug Playwright tests (flaky selectors, timeouts, auth flows). Dig into API check failures with packet captures (PCAPs), traceroutes and timing breakdowns. Set up single sign-on (SSO) and SAML. When it’s a bug, bring engineering a clean reproduction, or open the pull request (PR) yourself.
Build an outstanding AI support process. Our internal and external support agents already resolve 80% of tickets. You’ll help lift the bar: what the agent answers, when it hands off to a human, and how good those answers are.
Turn tickets into product. Spot patterns across customers and bring product and engineering a reproduction. Your work becomes bug fixes and features.
Own the docs. If you’ve answered something twice, it belongs in the docs and in the agent, so customers and AI get the same right answer.
Work with modern tooling. We are continuously updating our workbench, and you’ll have modern tools like Plain, Linear, and Mintlify.
This won't be the right role if you...
Want a clear process for every situation before you act.
Would rather code all day than talk to customers.
See AI tools as something you’ll get around to eventually.
