Support Engineer (DevTools & AI Reliability, remote)

Checkly builds developer tools for monitoring application reliability. The Support Engineer helps customers troubleshoot technical issues, improves AI-assisted support, turns customer feedback into product fixes and features, and maintains documentation.

Responsibilities:

• 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

Requirements:

• Some experience in a technical role, for example, as a developer or in technical support
• You can read and debug JavaScript, TypeScript and Node.js code
• You're comfortable with HTTP, REST APIs, browser dev tools, git and CI/CD practices
• AI is already how you work. Claude Code, Codex, Cursor or similar are part of your day
• You've built your own workflows
• You write and speak clear, friendly English
• You're based on the US East Coast or the same time zone