Support Engineer – DevTools, AI Reliability

atChecklyRemoteUS flagUnited StatesFull-timeSupport EngineerMid-levelSenior$57.5k – $70k/year

Posted Oct 29

This is a fully remote position, open to applicants in United States.

📋 Description

• Troubleshoot customer issues by analyzing Playwright tests and resolving API check failures.

• Conduct analysis of packet captures, traceroutes, and timing breakdowns.

• Configure single sign-on and SAML integrations.

• Provide the engineering team with clear bug reproductions or submit pull requests.

• Enhance the internal and external AI support agents along with their handoff processes.

• Recognize customer trends and convert support tickets into product enhancements and fixes.

• Manage and develop product documentation.

• Utilize contemporary support and productivity tools such as Plain, Linear, and Mintlify.

• Interact directly with customers and collaborate asynchronously with product and engineering teams.


⛳️ Requirements

• Some background in a technical position, such as development or technical support.

• Proficient in reading and debugging JavaScript, TypeScript, and Node.js code.

• Familiarity with HTTP, REST APIs, browser developer tools, Git, and CI/CD methodologies.

• Regular use of AI tools like Claude Code, Codex, Cursor, or comparable platforms.

• Proficient in clear and friendly written and spoken English.

• Capacity to work independently in a remote setting while collaborating with the team.

• Reside on the US East Coast or within the same time zone.

• Ability to debug Playwright tests, including issues with flaky selectors, timeouts, and authentication flows.

• Experience with API check failures, packet captures, traceroutes, and timing analyses.

• Experience in setting up SSO and SAML.


🏝️ Benefits

• Stock options.

• Flexible paid vacation.

• Paid sick leave.

• Up to 14 weeks of paid parental leave.

• Comprehensive medical, dental, and vision insurance in the US.

• Flexible Spending Account (FSA).

• Long-term and short-term disability insurance.

• Life insurance.

• 401(k) retirement plan.

• Annual company off-site events.

• Async-first, low-meeting work culture.

• Transparent salary structure.

• Access to modern tools including Plain, Linear, and Mintlify.

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