Remote AI Support Engineer - DevTools SaaS

Checkly Inc.; Atlanta, Boston, Philadelphia, Tampa (GA, MA, Philadelphia County, FL); Hybrid; USD 58,000 - 70,000; Full time

Job summary

Checkly Inc. is hiring a Support Engineer to help top customers in a remote, async-first setting. You’ll debug flaky Playwright tests, analyze API failures, and automate routine tasks with AI tools, while maintaining clear, helpful communication with customers.

Join a remote-first team that values lean processes, strong documentation, and collaboration with product, engineering, and support. Applicants should thrive in a customer-facing role and be comfortable working across time zones.

Qualifications

• You love helping customers and solving problems. Checkly is critical to them and you unblock them.
• Some experience in a technical role, e.g., developer or technical support.
• You can read and debug JavaScript, TypeScript and Node.js code.
• You’re comfortable with HTTP, REST APIs, browser dev tools, git and CI/CD practices.
• AI tools are part of your day (Claude Code, Codex, Cursor or similar).
• You write and speak clear, friendly English.

Responsibilities

• Resolve customer issues by debugging Playwright tests and API failures; set up SSO/SAML; provide clean reproduction or PR when bugs are found.
• Build an outstanding AI support process to improve agent handoffs and accuracy of answers.
• Turn tickets into product by spotting patterns and informing product/engineering with reproductions.
• Own the docs, ensuring consistency between agent answers and docs.
• Work with modern tooling and continuously update the workbench (Plain, Linear, Mintlify).

Skills

Empathy

Developer/Tech Support experience

Code reading: JavaScript/TypeScript/"/

HTTP/REST APIs & browser dev tools

Git & CI/CD practices

AI tooling (Claude Code, Codex, Cursor

Clear English communication

Remote work capability

US East Coast time zone awareness

Tools

Plain

Linear

Mintlify

Playwright

OpenTelemetry

Job description

Checkly Inc. is hiring a Support Engineer to help top customers in a remote, async-first setting. You’ll debug flaky Playwright tests, analyze API failures, and automate routine tasks with AI tools, while maintaining clear, helpful communication with customers.

Join a remote-first team that values lean processes, strong documentation, and collaboration with product, engineering, and support. Applicants should thrive in a customer-facing role and be comfortable working across time zones.