Sales Engineer

(Remote, ET+/-1 (e.g. Boston, Argentina), Series B DevTools SaaS)

Join Checkly as a Sales Engineer and empower developers and agents to own and ensure application performance and reliability - from pull request to post-mortem!

Checkly is the active reliability layer for developers and agents. We unify testing, synthetic monitoring, and observability into a single AI-native workflow, so engineering teams (and the agents shipping alongside them) can catch issues before customers do.

Our platform is trusted by teams at Vercel, CrowdStrike, 1Password, Airbus, Mistral, ServiceNow, and Fastly. In 2024, we raised $20M in Series B funding from Balderton, CRV, and Accel to take things to the next level.

That’s where you come in. As a part of our Sales team, you’ll play a key role in expanding our reach, building relationships with engineering teams, and showing them why Checkly is the best solution out there.

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 a Sales Engineer to ensure our customers get the best out of Checkly.

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

• You will support prospects through technical evaluations alongside our senior CSE and sales team.

• You will help existing customers with technical questions, implementations, and adoption.

• 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 and Engineering.

What you should have

• Some professional experience in a technical, customer-adjacent role. That could be software engineering with meaningful customer interaction, technical consultancy, professional services, developer relations, or a similar path.

• 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 prospect environments, generating tailored demo 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 demos, 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.

• Located in the ET+/-1 time zones.

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

• 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

• $80k-$124k OTE for someone in a similar cost of market as Argentina.

• $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.