Support Engineer; DevTools & AI Reliability, remote

(Remote, US East Coast or the same time zone. Series B. Dev Tools SaaS. Synthetic monitoring. 40h/week)

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 Open Telemetry and Playwright, and versioned and reviewed like everything else that ships. From pull request to post-mortem, in one place.

AI agents are shipping more code than any team can review, and reliability is lagging behind. Checkly closes this gap.

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 Linked In, Citi, and 1

Password on that journey.

In 2024 we raised $20M in Series B funding from Balderton, CRV and Accel. We're a remote-first startup that is low on meetings, high on productivity, and always shipping. If you love actually listening to and working with customers, working async, and keeping it lean, you'll fit right in!

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.

Support has always been about solving real problems for real people. What's changing at Checkly is how we do it: AI lets us automate routine work and assist us with troubleshooting, so we can go deeper on hard cases and bring what customers tell us straight back to the product.

Here's where you come in:

• Resolve customer issues.
• Debug Playwright tests (flaky selectors, timeouts, auth flows).
• Dig into API check failures with packet captures (PCAPs), trace routes and timing breakdowns.
• Set 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. Our internal and external support agents already resolve 80% of tickets. You'll help lift the bar: what the agent answers, when it hands off to a human, and how good those answers are.

Turn tickets into product. Spot patterns across customers and bring product and engineering a reproduction. Your work becomes bug fixes and features.

Own the docs. If you've answered something twice, it belongs in the docs and in the agent, so customers and AI get the same right answer.

Work with modern tooling. We are continuously updating our workbench, and you'll have modern tools like Plain, Linear, and Mintlify.

This won't be the right role if you...Want a clear process for every situation before you act.

Would rather code all day than talk to customers.

See AI tools as som