Support Engineer – DevTools, AI Reliability
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Job Description
Support Engineer helping Checkly customers debug Playwright, APIs, and monitoring failures. Improving AI-assisted support and feeding customer insights into Checkly’s DevTools SaaS product.
Responsibilities:
- 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:
- 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:
- 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
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