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ChecklySupport Engineer (DevTools & AI Reliability, remote)
Checkly is hiring a Support Engineer (DevTools & AI Reliability) to join its remote team on the US East Coast or a matching time zone. Operating…
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About This Role
Checkly is hiring a Support Engineer (DevTools & AI Reliability) to join its remote team on the US East Coast or a matching time zone. Operating as a Series B developer-tools SaaS company, Checkly provides synthetic monitoring solutions driven by OpenTelemetry and Playwright, allowing AI agents and developers to build, run, and maintain production monitoring as code. The company recently secured $20 million in Series B financing and maintains a…
Job Description
Checkly is hiring a Support Engineer (DevTools & AI Reliability) to join its remote team on the US East Coast or a matching time zone. Operating as a Series B developer-tools SaaS company, Checkly provides synthetic monitoring solutions driven by OpenTelemetry and Playwright, allowing AI agents and developers to build, run, and maintain production monitoring as code. The company recently secured $20 million in Series B financing and maintains a remote-first work environment characterized by minimal meetings and asynchronous communication.
In this full-time role of 40 hours per week, the support engineer will guide prominent customers—ranging from modern AI enterprises to large engineering organizations—through technical troubleshooting and product usage. The position combines customer engagement with AI tooling, debugging, and documentation maintenance, requiring familiarity with modern developer workflows and asynchronous collaboration.
Responsibilities
- Address and resolve customer technical issues, including debugging Playwright tests involving flaky selectors, timeouts, and authentication workflows
- Investigate API check failures using traceroutes, packet captures, and timing breakdowns
- Configure single sign-on and SAML for users
- Prepare clean reproductions or create pull requests for software bugs discovered during troubleshooting
- Enhance artificial intelligence support procedures by refining automated answers and escalation protocols
- Identify cross-customer patterns and translate them into actionable bug reports or product feature requests
- Maintain documentation and update AI agent knowledge bases with accurate solutions
- Utilize modern workbench software such as Plain, Linear, and Mintlify
Requirements
- Prior technical work experience, such as a developer or technical support role
- Ability to read and debug Node.js, TypeScript, and JavaScript code
- Familiarity with REST APIs, HTTP, git, browser developer tools, and continuous integration and continuous delivery practices
- Practical daily usage of AI tools like Cursor, Codex, or Claude Code
- Proficiency in written and spoken English
- Ability to operate independently in a remote setting
- Location on the US East Coast or an identical time zone
Core Skills
Benefits
- Transparent compensation determined by a standardized salary calculator
- Stock options
- Flexible paid vacation
- Paid sick leave
- Up to 14 weeks of paid parental leave
- Medical, dental, and vision coverage
- Flexible spending account
- Long-term and short-term disability insurance
- Life insurance
- 401(k) plan
- Annual company off-site gatherings
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
What is the remote work policy for this position?
This is a remote position requiring candidates to be based on the US East Coast or an identical time zone.
What is the salary range for this role?
The salary range for this role is USD 57,500 to 70,000 per year for standard US locations, with adjustments for specific tiers like NYC and Boston, or international locations such as South America.
What are the core technical skills needed for this job?
Candidates must be able to read and debug JavaScript, TypeScript, and Node.js, and be comfortable with HTTP, REST APIs, browser dev tools, git, and CI/CD practices.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.