Associate Support Engineer (DevTools & AI Reliability) - Checkly

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.

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

We’re a remote-first startup that keeps things simple—low on meetings, high on productivity, and always shipping. If you love working with customers, working async, and keeping it lean, you’ll fit right in!

What You’ll Do

We're looking for an Associate Support Engineer to help developers and their AI agents ensure the stability of their web apps and APIs for end-users. You will report to our Chief Commercial Officer (CCO).

You will be responsible for addressing our end-users' complex technical problems. Specifically, you will:

• Advise customers on solving complex technical challenges by diving deep into code:
  • 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 assist with role and permission setup
• Act as the first point of contact for customer technical requests
• Investigate and reproduce reported issues
• Work closely with product and engineering teams to solve customer problems and improve Checkly
• Contribute to support processes and documentation
• Help develop and refine Checkly's AI support agents

What You Should Have

• Initial work experience in a technical role (e.g., developer, support engineer)
• Strong technical skills allowing you to debug code (JavaScript/Node.js preferred)
• Familiarity with core web technologies (HTTP, REST, Chrome DevTools)
• Basic understanding of SDLC, CI/CD practices, and source control (Git)
• Empathy and a passion for working directly with customers to solve problems
• Ability to leverage modern AI tools (Claude Code, Codex, etc.) to accelerate work
• Excellent written English communication skills
• Autonomous and self-motivated in a remote, async environment
• Strong attention to detail
• Based on the US East Coast or in a matching time zone (e.g., Eastern Time / LATAM)

Why Us?

• Transparent salary framework based on location and experience
• Flexible work hours and an async-first culture (low meetings, high output)
• Fast-growing, international startup where your work directly impacts the product
• Stock options
• Flexible paid vacation and paid sick leave
• Up to 14 weeks of paid parental leave
• US Benefits: Medical, Dental, Vision, FSA, short/long-term disability, life insurance, and 401(k)
• Annual company off-site