Support Engineer (DevTools & AI Reliability, remote)

Checkly; Tampa (FL); Remote; USD 43,000 - 87,000; Full time

Benefits offered by this job

Stock options

Flexible paid vacation

Paid sick leave & up to 14 weeks ofPar

Job summary

Checkly, a remote-first DevTools SaaS, is hiring a Support Engineer to help our customers, from AI startups to large engineering teams, in a fast-paced, async environment.

You’ll diagnose issues in Playwright tests, debug API check failures, and contribute to docs and onboarding, turning tickets into product improvements.

This role emphasizes empathy, customer collaboration, and a lean, transparent pay culture, with flexible vacation and stock options.

Qualifications

• Experience in a technical role, eg. developer or technical support.
• Ability to read and debug JavaScript, TypeScript and Node.js code.
• Familiarity with HTTP/REST APIs, browser dev tools, git and CI/CD practices.
• Knowledge of AI tooling and building automated workflows.

Responsibilities

• Resolve customer issues and debug Playwright tests (flaky selectors, timeouts, auth flows).
• Investigate API check failures with PCAPs, traceroutes, timing breakdowns; set up SSO/SAML.
• Turn tickets into product improvements and reproduce bugs for engineering.
• Own the docs; ensure consistent customer answers across humans and AI agents.
• Work with tooling like Plain, Linear, and Mintlify.

Skills

Empathy

Technical experience

JavaScript/TypeScript/Node.js

HTTP/REST APIs

CI/CD practices

AI tooling familiarity

English communication

Remote work capability

US East Coast time zone

Tools

Git

CI/CD tools

Job description

(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 environment with inclusive benefits and full transparency about how we pay.

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. 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 something you’ll get around to eventually.
• Want the structure and pace of a large company.

What you should have

• 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 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’ve 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.
• You're based on the US East Coast or the same time zone.

Why us?

• Transparent salary because your salary shouldn't 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.

What we pay

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

• $57,500 - $70,000 for someone in the US
• $71,910 - $87,000 for someone in US Tier 1 locations like NYC, Boston
• $43,000 - $52,000 for someone in e.g. South America

Compensation Range: $43,000 - $87,000