Remote AI Support Engineer — DevTools SaaS

Checkly; Boston (KY); Remote; USD 58,000 - 87,000; Full time

Benefits offered by this job

Transparent salary

Async culture

Stock options

Flexible vacation

Parental leave 14 weeks

US health benefits

Annual off-site

Job summary

Checkly is a remote-first DevTools SaaS company focused on synthetic monitoring. As a Support Engineer, you’ll help customers like Mistral and LinkedIn, debug Playwright tests, set up SSO, and improve our support processes.

Join a lightweight, async-friendly team with transparent pay and benefits, including parental leave and health coverage. You’ll work from the US East Coast or the same time zone, 40 hours per week, and ship reliable support at scale.

Qualifications

• Empathize with customers and unblock issues promptly.
• Experience in a technical role (developer or tech support).
• Ability to read and debug JavaScript/TypeScript/Node.js code.
• Comfort with HTTP, REST APIs, browser dev tools, Git and CI/CD practices.
• AI tooling familiarity (Claude Code, Codex, Cursor or similar).
• Clear written and spoken English communication.
• Ability to work remotely and collaborate asynchronously.
• Based on US East Coast or the same time zone.

Responsibilities

• Resolve customer issues and debug Playwright tests (flaky selectors, timeouts, auth flows).
• Build an outstanding AI-supported support process and improve agent handoffs.
• Turn tickets into product: reproduce bugs and coordinate with engineering.
• Own the documentation so answers are in docs and in the agent.
• Work with modern tooling such as Plain, Linear, and Mintlify.

Skills

Customer empathy

Technical support

JavaScript

TypeScript

Node.js

HTTP/REST

CI/CD

AI tooling

English communication

Remote work

Time zone US East

Job description

Checkly is a remote-first DevTools SaaS company focused on synthetic monitoring. As a Support Engineer, you’ll help customers like Mistral and LinkedIn, debug Playwright tests, set up SSO, and improve our support processes.

Join a lightweight, async-friendly team with transparent pay and benefits, including parental leave and health coverage. You’ll work from the US East Coast or the same time zone, 40 hours per week, and ship reliable support at scale.