[Hiring] Support Engineer @Checkly

Role Description

The best developers don’t wait for a customer to tell them something’s broken. They catch it first, in the pull request, in staging, or in the checkout flow at 3am, before a single user notices. That instinct is Checkly’s whole reason to exist. Now that agents write and ship more and more code, they can carry that instinct too. Agents write, run, and maintain the monitoring setup that guards production, while developers stay in control. Everything is defined as code, powered by OpenTelemetry and Playwright, and versioned and reviewed like everything else that ships. From pull request to post-mortem, in one place.

As a Support Engineer, you’ll support our most valuable customers, from modern AI companies like Mistral and resolve.ai to large engineering orgs like LinkedIn, Citi, and 1Password on that journey.

What you’ll do:

• Resolve customer issues.
• Debug Playwright tests (flaky selectors, timeouts, auth flows).
• Dig into API check failures with packet captures (PCAPs), traceroutes, and timing breakdowns.
• Set up single sign-on (SSO) and SAML.
• Bring engineering a clean reproduction or open the pull request (PR) yourself when it’s a bug.
• Build an outstanding AI support process.
• Turn tickets into product.
• Own the docs.
• Work with modern tooling.

Qualifications

• Empathy: You love working with customers and solving their problems.
• Some experience in a technical role, for example, as a developer or in 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 is already how you work. Claude Code, Codex, Cursor, or similar are part of your day.
• You write and speak clear, friendly English.
• You can run your own day remotely and still enjoy working with your team.
• You're based on the US East Coast or the same time zone.

Requirements

• Want a clear process for every situation before you act.
• Would rather code all day than talk to customers.
• See AI tools as something you’ll get around to eventually.
• Want the structure and pace of a large company.

Benefits

• Transparent salary because your salary shouldn't be dictated by how good a negotiator you are.
• Async-first (low meeting, high productivity) and transparent culture.
• Stock options.
• Flexible paid vacation.
• Paid sick leave & 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.

Company Description

We care about building a team where people of all backgrounds are encouraged to do their best work. To achieve this we built a flexible and async-first startup environment with inclusive benefits and full transparency about how we pay.