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Checkly

Support Engineer – DevTools, AI Reliability

Checkly

. Resolve customer issues by debugging Playwright tests and API check failures .

Posted 10/28/2026full-timeRemote • United StatesMid-LevelSenior💰 $57,500 - $70,000 per yearWebsite

Core Competencies

Role fit
Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in debugging Playwright tests and API failures, with strong capabilities in analyzing network data and implementing single sign-on solutions. Proficient in collaborating with engineering teams to enhance product features and documentation while utilizing modern support tools.

Highest-signal resume keywords
Debugging Playwright TestsJavaScript ProficiencyAPI Check FailuresSingle Sign-On (SSO) SetupAI Tools Experience

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
JavaScriptTypeScriptNode.jsHTTPREST APIsGitCI/CD PracticesPacket Capture AnalysisTraceroute AnalysisDebugging Techniques
Soft Skills
Clear CommunicationFriendly InteractionIndependent WorkCollaboration
Tools & Technologies
PlaywrightPlainLinearMintlifyClaude CodeCodexCursor
Industry Keywords
Technical SupportProduct DocumentationCustomer Issue ResolutionAI Support AgentsAsynchronous Collaboration

Tech Stack

Tools & technologies
JavaScriptNode.jsTypeScript

About the role

Key responsibilities & impact
  • Resolve customer issues by debugging Playwright tests and API check failures
  • Analyze packet captures, traceroutes, and timing breakdowns
  • Set up single sign-on and SAML
  • Provide engineering with clean bug reproductions or open pull requests
  • Improve internal and external AI support agents and their handoff processes
  • Identify customer patterns and turn support tickets into product fixes and features
  • Maintain and expand product documentation
  • Use modern support and productivity tools such as Plain, Linear, and Mintlify
  • Work directly with customers and collaborate asynchronously with product and engineering

Requirements

What you’ll need
  • Some experience in a technical role, such as development or technical support
  • Ability to read and debug JavaScript, TypeScript, and Node.js code
  • Comfortable with HTTP, REST APIs, browser developer tools, Git, and CI/CD practices
  • Daily use of AI tools such as Claude Code, Codex, Cursor, or similar
  • Clear, friendly written and spoken English
  • Ability to work independently remotely and collaborate with the team
  • Based on the US East Coast or in the same time zone
  • Ability to debug Playwright tests, including flaky selectors, timeouts, and authentication flows
  • Experience with API check failures, PCAPs, traceroutes, and timing breakdowns
  • Experience setting up SSO and SAML

Benefits

Comp & perks
  • Stock options
  • Flexible paid vacation
  • Paid sick leave
  • Up to 14 weeks of paid parental leave
  • US medical, dental, and vision insurance
  • FSA
  • Long- and short-term disability insurance
  • Life insurance
  • 401(k)
  • Annual company off-site
  • Async-first, low-meeting work culture
  • Transparent salary
  • Modern tools including Plain, Linear, and Mintlify