Support Engineer (DevTools & AI Reliability, remote)

About this role

Support developers using Checkly’s synthetic monitoring platform to identify and resolve application reliability issues. The role combines technical troubleshooting, customer support, AI-assisted support process improvement, and feedback that informs product development.

About the company

Checkly provides a platform for monitoring and improving the performance of web applications and APIs. The company focuses on delivering solutions that empower developers and operations teams to ensure their systems are running smoothly and meeting user expectations.

The team

Customer department

Stack

What you'll do

• Troubleshoot customer issues, including Playwright tests, API checks, SSO, and SAML.
• Create clear bug reproductions and contribute fixes through pull requests when appropriate.
• Improve AI support agents’ answers, escalation decisions, and overall quality.
• Identify customer issue patterns and share actionable feedback with product and engineering.
• Maintain documentation and ensure support agents can provide accurate answers.

What we're looking for

• 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.
• Regular use of AI tools such as Claude Code, Codex, or Cursor, with established workflows.
• Strong customer empathy and clear written and spoken English.
• Able to work independently in a remote setting.
• Located in the US Eastern Time zone.

Benefits

• Stock options
• Flexible paid vacation
• Paid sick leave and up to 14 weeks of paid parental leave
• US medical, dental, and vision coverage, FSA, disability and life insurance, and 401(k)
• Annual company off-site