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 dont wait for a customer to tell them somethings 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 Checklys 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 youll support our most valuable customers from modern AI companies like Mistral and 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. Were 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 youll 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. Whats 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. Heres where you come in:

• 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. When its 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. Youll 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 youve 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 youll have modern tools like Plain Linear and Mintlify.

• Want a clear process for every situation before you act.

• Would rather code all day than talk to customers.

• See AI tools as something youll get around to eventually.

• Want the structure and pace of a large company.

You will often speak with developers who need assistance understanding if their applications work well and if not what caused the issue. This requires a solid technical background and a genuine motivation to help and learn.

• Empathy: You love working with customers and solving their problems. Checkly is critical to them and we genuinely want to unblock them.

• Some experience in a technical role for example as a developer or in technical support.

• You can read and debug JavaScript TypeScript and code.

• Youre 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. Youve built your own workflows.

• You write and speak clear friendly English.

• You can run your own day remotely and still enjoy working with your team.

• Youre based on the US East Coast or the same time zone.

• Transparent salary because your salary shouldnt be dictated by how good a negotiator you are. (more info below)

• 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

Find out more here.

Fair competitive and transparent pay is very important for us. Therefore we work with a standardized salary calculator that includes several factors such as seniority level as well as location.

For this role the range is

• $57500 - $70000 for someone in the US

• $71910 - $87000 for someone in US Tier 1 locations like NYC Boston

• $43000 - $52000 for someone in e.g. South America

If this sounds interesting please apply! Studies by several different sources have shown that on average men will apply for a job if they meet 60% of the application requirements. Women non-binary people and POC will seek to match a much higher percentage of requirements before applying. If youre not sure youre the right fit apply anyway and let us know what you bring to the table. Wed love to hear from you!

Were all about being transparent and setting clear expectations. Thats why weve put together our hiring playbook and open-sourced our employee handbook. There youll find a sneak peek of who we are how we work and what you can expect in our hiring process.

Required Experience:

IC