Support Engineer (DevTools & AI Reliability, remote)

(Remote, US East Coast or the same time zone. Series B. DevTools 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 OpenTelemetry 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 LinkedIn, Citi, and 1Password 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 environme