Associate 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. We give developers and their agents the tools to own reliability the way they own their code: end-to-end tests and synthetic monitoring defined as code, powered by OpenTelemetry and Playwright, versioned and reviewed like everything else they ship. From pull request to post-mortem, in one place.

Thousands of them, from modern AI companies like Mistral and resolve.ai to large engineering orgs like LinkedIn, Citi, and 1Password, build with us. In 2024 we raised $20M in Series B funding from Balderton, CRV and Accel.

AI agents and coding assistants are shipping more software, faster, than any team could review by hand, and more of it is breaking in ways nobody has seen before. LLM-backed features fail probabilistically. Agents take actions no runbook anticipated. "Is my app healthy?" is becoming an unanswerable question for a whole generation of AI-native software. You will help Engineers and their Agents to own and ensure application performance and reliability.

We’re a remote-first startup that keeps things simple—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

We're looking for an Associate Support Engineer to help developers and their agents, who rely on Checkly, to ensure the stability of their web apps and APIs for their end-users. We care a lot about our customers and our interaction with them. You will report to Timo, our CCO.

You will be responsible for addressing our end-users' complex problems. In detail you will:

• Advise customers how to solve complex technical challenges, diving deep into code, for example:
  • Debug Playwright test scripts (flaky selectors, timeouts, auth flows, etc.)
  • Troubleshoot API Check failures using PCAPs, traceroutes and response timing breakdowns
  • Debug setup/teardown scripts and request handling in API Checks
  • Configure SSO/SAML and help with role and permission setup
• Be the first point of contact for customer requests
• Investigate and reproduce issues
• Work closely with the product and engineering teams to solve customer problems and look for ways to improve Checkly
• Contribute to support processes going forward
• Contribute to and update the Checkly docs
• Contribute to developing Checkly's AI support agents further

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 deep technical background and a genuine motivation to help and learn.

• Initial work experience in a technical role e.g. developer
• Strong technical skills that allow you to debug code (Javascript/Node.js preferred).
• Familiarity with web technologies (HTTP, REST, Chrome DevTools)
• Basic understanding of SDLC, CI/CD practices, source control (git)
• Empathy: you enjoy working with customers and solving their problems
• Ability to use AI tools to accelerate work. We build with Claude Code, Codex, and similar tools. We just finished the first phase of our AI Support project to help you unblock customers even faster.
• Excellent written English skills
• Ability to be autonomous and self-motivated in a remote work environment, while you also enjoy getting to know your colleagues and helping others
• Attention to detail
• 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)
• Flexible work hours, async-first (low meeting, high productivity) and transparent culture
• Become part of a fast-growing, and international team where your work matters—your impact won’t get lost in layers of bureaucracy.
• 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

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.