Remote AI Support Engineer — DevTools SaaS

Checkly; Tampa (FL); Remote; USD 43,000 - 87,000; Full time

Benefits offered by this job

Stock options

Flexible paid vacation

Paid sick leave & up to 14 weeks ofPar

Job summary

Checkly, a remote-first DevTools SaaS, is hiring a Support Engineer to help our customers, from AI startups to large engineering teams, in a fast-paced, async environment.

You’ll diagnose issues in Playwright tests, debug API check failures, and contribute to docs and onboarding, turning tickets into product improvements.

This role emphasizes empathy, customer collaboration, and a lean, transparent pay culture, with flexible vacation and stock options.

Qualifications

• Experience in a technical role, eg. developer or technical support.
• Ability to read and debug JavaScript, TypeScript and Node.js code.
• Familiarity with HTTP/REST APIs, browser dev tools, git and CI/CD practices.
• Knowledge of AI tooling and building automated workflows.

Responsibilities

• Resolve customer issues and debug Playwright tests (flaky selectors, timeouts, auth flows).
• Investigate API check failures with PCAPs, traceroutes, timing breakdowns; set up SSO/SAML.
• Turn tickets into product improvements and reproduce bugs for engineering.
• Own the docs; ensure consistent customer answers across humans and AI agents.
• Work with tooling like Plain, Linear, and Mintlify.

Skills

Empathy

Technical experience

JavaScript/TypeScript/Node.js

HTTP/REST APIs

CI/CD practices

AI tooling familiarity

English communication

Remote work capability

US East Coast time zone

Tools

Git

CI/CD tools

Job description

Checkly, a remote-first DevTools SaaS, is hiring a Support Engineer to help our customers, from AI startups to large engineering teams, in a fast-paced, async environment.

You’ll diagnose issues in Playwright tests, debug API check failures, and contribute to docs and onboarding, turning tickets into product improvements.

This role emphasizes empathy, customer collaboration, and a lean, transparent pay culture, with flexible vacation and stock options.