(Remote, US East Coast, Series B DevTools SaaS, synthetic monitoring)

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.

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.

That’s where you come in. 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.

What you’ll do

We're looking for a Solutions Engineer to make sure customers get real value out of Checkly after they sign.

• You will learn Checkly and the monitoring space deeply, then help customers solve real reliability problems.

• You will own technical onboarding for new accounts: implementation, configuration, and getting their first monitoring into production.

• You will run workshops and trainings for customer engineering teams.

• You will be the technical counterpart in existing accounts, supporting adoption, troubleshooting, and growth alongside the sales team.

• You will run your own customer meetings, from technical deep dives to account check-ins.

• You will contribute to technical documentation and internal playbooks as you learn what works.

• You will speak with customers directly and share your learnings with Product Engineering and Marketing.

What you should have

• Around 2 years of experience in a post-sales technical role: customer onboarding, workshops and trainings, and helping accounts grow. Solutions engineering, professional services, customer success engineering, technical account management, or a similar path all work.

• 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: researching a customer's stack, generating tailored example code, building proof-of-concept repos, drafting technical responses. We build with Claude Code, Codex, and similar tools.

• Genuine interest in working directly with customers. You enjoy talking to people, running workshops and demos, driving a meeting yourself, and explaining technical concepts clearly.

• Excellent spoken and written English skills

• Ability to be autonomous and self-motivated in an async-work environment, while you also enjoy getting to know your colleagues and helping others.

• Based on the US East Coast, in Eastern Time (ET).

• Able to travel occasionally to customers.

• Startup experience is helpful, but not required.

Why us?

• Transparent salary (more info below)

• 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 on-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, 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.

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.