[Hiring] Solutions Engineer @Checkly

Role Description

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.

Here's the thing about 2026: 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.

This role starts where the sale ends. You will onboard new customers, train their engineering teams, and stay close to those accounts as their use of Checkly grows. You are the technical counterpart in the account, and you run your own customer meetings.

• Onboard new customers and train their engineering teams.
• Own technical onboarding for new accounts: implementation, configuration, and getting their first monitoring into production.
• Run workshops and trainings for customer engineering teams.
• Support adoption, troubleshooting, and growth alongside the sales team.
• Run your own customer meetings, from technical deep dives to account check-ins.
• Contribute to technical documentation and internal playbooks.
• Speak with customers directly and share learnings with Product Engineering and Marketing.

Qualifications

• Around 2 years of experience in a post-sales technical role: customer onboarding, workshops and trainings, and helping accounts grow.
• Hands-on experience with monitoring, observability, or automated testing.
• Strong technical skills that allow you to read, write, and debug code (Javascript/Node.js preferred).
• Ability to use AI tools to accelerate customer-facing work.
• Genuine interest in working directly with customers.
• Excellent spoken and written English skills.
• Ability to be autonomous and self-motivated in an async-work environment.
• Based on the US East Coast, in Eastern Time (ET).
• Able to travel occasionally to customers.
• Startup experience is helpful, but not required.

Benefits

• Transparent salary.
• Become part of a fast-growing, and international team where your work matters.
• 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 on-site.

Company Description

For this role, there’s a 70% base salary - 30% commission split. The range is $107k-$155k OTE for someone in the US. $134k-$185k OTE for someone in US Tier 1 locations like NYC, Boston.

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.