Support Engineer (DevTools & AI Reliability, remote)

Checkly•Raleigh, NC

15h•Remote

About The Position

Checkly is hiring a Support Engineer to help customers use its developer tools and synthetic monitoring platform. The role supports customers ranging from AI companies to large engineering organizations, resolving technical issues and bringing customer insights back to the product. Checkly is a remote-first, async-first startup that uses AI to automate routine support work so the team can focus on complex cases and improve the customer experience. The role works with modern support and documentation tools, including Plain, Linear, and Mintlify.

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.
Regular use of AI tools such as Claude Code, Codex, Cursor, or similar, and experience building personal workflows with them.
Clear, friendly written and spoken English.
Ability to manage work remotely and collaborate with a team.
Based on the US East Coast or in the same time zone.
Empathy, genuine interest in helping customers, and motivation to learn.

Responsibilities

Resolve customer issues, including debugging Playwright tests and investigating API check failures using packet captures, traceroutes, and timing breakdowns.
Configure single sign-on (SSO) and SAML for customers.
Provide engineering with clear bug reproductions or contribute fixes by opening pull requests.
Improve the AI support process by refining what support agents answer, when they escalate to a human, and the quality of their responses.
Identify patterns in customer tickets and share reproductions with product and engineering teams to inform bug fixes and features.
Maintain documentation and ensure recurring answers are captured in both documentation and the support agent.
Work with modern support and development tools, including Plain, Linear, and Mintlify.