Associate Support Engineer (DevTools & AI Reliability, remote)

Checkly is hiring an Associate Support Engineer to help developers and their agents ensure the stability of web apps and APIs. The role focuses on resolving technical customer issues, collaborating with product and engineering, improving support processes and documentation, and contributing to AI support agents.

Responsibilities:

• Advise customers how to solve complex technical challenges, diving deep into code, for example:
• Debug Playwright test scripts (flaky selectors, timeouts, auth flows, etc.)
• Troubleshoot API Check failures using PCAPs, traceroutes and response timing breakdowns
• Debug setup/teardown scripts and request handling in API Checks
• Configure SSO/SAML and help with role and permission setup
• Be the first point of contact for customer requests
• Investigate and reproduce issues
• Work closely with the product and engineering teams to solve customer problems and look for ways to improve Checkly
• Contribute to support processes going forward
• Contribute to and update the Checkly docs
• Contribute to developing Checkly's AI support agents further

Requirements:

• Initial work experience in a technical role e.g. developer
• Strong technical skills that allow you to debug code
• Familiarity with web technologies (HTTP, REST, Chrome DevTools)
• Basic understanding of SDLC, CI/CD practices, source control (git)
• Empathy: you enjoy working with customers and solving their problems
• Ability to use AI tools to accelerate work
• Excellent written English skills
• Ability to be autonomous and self-motivated in a remote work environment, while you also enjoy getting to know your colleagues and helping others
• Attention to detail
• Javascript/Node.js preferred