Support Engineer (DevTools & AI Reliability, remote)

Checkly is a DevTools SaaS company offering synthetic monitoring, where agents write, run and maintain monitoring setup defined as code, powered by OpenTelemetry and Playwright. The Support Engineer will support customers such as Mistral, resolve.ai, LinkedIn, Citi and 1Password, resolve customer issues, build an AI support process, turn tickets into product, and own the docs. The company raised $20M in Series B funding from Balderton, CRV and Accel in 2024 and is a remote-first startup. Pay ranges: $57,500 - $70,000 for someone in the US; $71,910 - $87,000 for someone in US Tier 1 locations like NYC and Boston; $43,000 - $52,000 for someone in e.g. South America.

Responsibilities

Resolve customer issues, including debugging Playwright tests (flaky selectors, timeouts, auth flows), investigating API check failures with packet captures (PCAPs), traceroutes and timing breakdowns, and setting up single sign-on (SSO) and SAML; When it's a bug, bring engineering a clean reproduction or open the pull request (PR) yourself; Build an outstanding AI support process by helping the support agents answer correctly, decide when to hand off to a human, and improve answer quality; Turn tickets into product by spotting patterns across customers and bringing product and engineering a reproduction; Own the docs by moving repeatedly answered questions into the docs and the agent; Work with modern tooling such as Plain, Linear and Mintlify

Requirements

Some experience in a technical role, for example, as a developer or in technical support; Empathy and a love of working with customers and solving their problems; Can read and debug JavaScript, TypeScript and Node.js code; Comfortable with HTTP, REST APIs, browser dev tools, git and CI/CD practices; Uses AI tools in daily work (e.g., Claude Code, Codex, Cursor or similar) and has built own workflows; Writes and speaks clear, friendly English; Can run own day remotely and enjoy working with a team; Based on the US East Coast or in the same time zone

Benefits

Transparent salary; Async-first, low-meeting work environment and transparent culture; Stock options; Flexible paid vacation; Paid sick leave and up to 14 weeks of paid parental leave; US: Medical, Dental, Vision, FSA, long- and short-term disability, life insurance, 401(k) and more; Annual company off-site