Support Engineer (DevTools & AI Reliability, remote)

Checkly•Raleigh, NC

2d•$43,000 - $87,000•Remote

About The Position

Checkly is hiring a Support Engineer to help customers use its developer tools and AI-powered synthetic monitoring platform. The role supports valuable customers, including AI companies and large engineering organizations, by investigating technical issues and bringing customer feedback back to product and engineering teams. Support work includes debugging Playwright tests and API check failures, configuring SSO and SAML, and providing engineering with clear reproductions of bugs. The engineer will also improve Checkly’s AI support process, identify recurring customer issues that can become product fixes or features, and maintain documentation so customers and AI agents can find reliable answers. The role uses current support and development tools such as Plain, Linear, and Mintlify. Checkly is a remote-first, async-first startup with a low-meeting, high-productivity culture. The position is remote for someone based on the US East Coast or in the same time zone. The stated work schedule is 40 hours per week.

Requirements

Some experience in a technical role, such as development or technical support.
Ability to read and debug JavaScript, TypeScript, and Node.js code.
Comfort with HTTP, REST APIs, browser developer tools, git, and CI/CD practices.
Practical use of AI tools such as Claude Code, Codex, Cursor, or similar, including building personal workflows.
Clear, friendly written and spoken English.
Ability to manage work remotely while enjoying collaboration with the team.
Based on the US East Coast or in the same time zone.
Empathy, motivation to help customers solve problems, and willingness to learn.

Responsibilities

Resolve customer issues by debugging Playwright tests, investigating API check failures, and configuring SSO and SAML.
Provide engineering with clean reproductions of bugs and, where appropriate, open a pull request to address them.
Improve the internal and external AI support process, including what agents answer, when they hand off to a human, and the quality of their answers.
Identify patterns in customer tickets and bring reproductions and insights to product and engineering teams.
Maintain documentation and ensure recurring answers are available to customers and the AI support agent.
Use modern support and workbench tools, including Plain, Linear, and Mintlify.