Support Engineer (DevTools & AI Reliability, remote)
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Before you apply
Salary$43k – $87k
LocationEastern Time zone
Work moderemote · United States
Typefull-time
SeniorityMid
DepartmentCustomer
EquityIncluded
Company size11–50 people
PostedOct 28, 2026 · 1w ago
Verified live3d ago
At a glanceSummarised by Seekless from the posting.
Empathy: love working with customers and solving their problems
Some experience in a technical role, for example, as a developer or in technical support
Can read and debug JavaScript, TypeScript and Node.js code
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)
Write and speak clear, friendly English
Can run your own day remotely and still enjoy working with your team
Based on the US East Coast or the same time zone
Skills
JavaScript
TypeScript
Node.js
HTTP
REST APIs
browser dev tools
git
CI/CD
Playwright
OpenTelemetry
SAML
SSO
Plain
Linear
Mintlify
Claude Code
Codex
Cursor
Benefits
Stock options
Flexible vacation
Paid sick leave
Parental leave
Health insurance
Dental insurance
Vision insurance
FSA
Disability insurance
Life insurance
401(k)
About the role
(Remote, US East Coast or the same time zone. Series B. DevTools SaaS. Synthetic monitoring. 40h/week)
About the company
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
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:
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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.
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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.
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Turn tickets into product. Spot patterns across customers and bring product and engineering a reproduction. Your work becomes bug fixes and features.
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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.
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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…
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Want a clear process for every situation before you act.
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Would rather code all day than talk to customers.
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See AI tools as something you’ll get around to eventually.
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Want the structure and pace of a large company.
What you should have
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.
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Empathy: You love working with customers and solving their problems. Checkly is critical to them, and we genuinely want to unblock them.
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Some experience in a technical role, for example, as a developer or in technical support.
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You can read and debug JavaScript, TypeScript and Node.js code.
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You’re comfortable with HTTP, REST APIs, browser dev tools, git and CI/CD practices.
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AI is already how you work. Claude Code, Codex, Cursor or similar are part of your day. You’ve built your own workflows.
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You write and speak clear, friendly English.
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You can run your own day remotely and still enjoy working with your team.
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You’re based on the US East Coast or the same time zone.
Why us?
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Transparent salary because your salary shouldn’t be dictated by how good a negotiator you are. (more info below)
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Async-first (low meeting, high productivity) and transparent culture
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Stock options
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Flexible paid vacation
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Paid sick leave & up to 14 weeks of paid parental leave
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US: Medical, Dental, Vision, FSA, long- and short-term disability, life insurance, 401(k) and more
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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
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$57,500 - $70,000 for someone in the US
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$71,910 - $87,000 for someone in US Tier 1 locations like NYC, Boston
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$43,000 - $52,000 for someone in e.g. South America
Apply
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 you’re not sure you’re the right fit, apply anyway and let us know what you bring to the table. We’d love to hear from you!
We’re all about being transparent and setting clear expectations. That’s why we’ve put together our hiring playbook and open-sourced our employee handbook. There you’ll find a sneak peek of who we are, how we work and what you can expect in our hiring process.
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