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Senior Sales Engineer (Pre-Sales) (USA, remote, ET or CT)

April 28, 2026

(Remote with option to go to NYC office if convenient, ET or CT, Series B DevTools SaaS)Join <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.checklyhq.com/">Checkly</a> as a Senior Sales Engineer (Pre-Sales) and empower developers and agents to own and ensure application performance and reliability - from pull request to post-mortem!Checkly helps engineers build reliable products by unifying testing, synthetic monitoring and observability. OpenTelemetry, Playwright, and Monitoring as Code are our foundation for unifying performance and reliability.Our platform is already trusted by teams at Vercel, LinkedIn, 1Password, CrowdStrike and Render, but we’re just getting started. In 2024, we raised <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.checklyhq.com/blog/announcing-20m-to-enable-engineers-to-detect-and-r/">$20M in Series B</a> 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. If you thrive in an entrepreneurial environment and love closing deals that genuinely help developers, this is the place for you.We care about building a team where people of all backgrounds are encouraged to do their best work. To achieve this we built a <a target="_blank" rel="noopener noreferrer nofollow" href="https://blog.checklyhq.com/how-to-build-a-leading-remote-first-company-while-exceeding-company-goals-do-this/">flexible and async-first</a> startup environment with <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.notion.so/Benefits-Perks-ad474bec3a5d4d17bfbb43ebae3fec9c?pvs=21">inclusive benefits</a> and full transparency about how we pay.<h2>What you’ll do</h2>We're looking for a Senior Sales Engineer to ensure our customers get the best out of Checkly. You will be part of the Checkly Customer Organization and will report to <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.linkedin.com/in/tonymerlino/">Tony</a>, our Chief Revenue Officer.<ul style="min-height:1.5em"><li>You will become an expert on Checkly and the Monitoring space, helping drive the Monitoring as Code revolution, and solve real customer problems.</li><li>You will work with some of our most valuable customers in different stages across pre-sales.</li><li>You will assist prospects with the technical evaluation of Checkly, from first demo to the successful implementation of Checkly. You will own this process.</li><li>You will speak with our customers directly and share your learnings with Product and Engineering, helping shape Checkly.</li><li>As part of your role you will assist in continuously improving technical documentation, processes and policies.</li><li>During your onboarding you will be involved in our Customer Support to learn our platform inside out and understand our customers. After that, you will chip in Support when needed from time to time.</li></ul><h2>What you should have</h2><ul style="min-height:1.5em"><li>Strong technical skills that allow you to read, write and debug code (Javascript/Node.js preferred).</li><li>Relevant experience working in a Solutions Engineering role, ideally in dev-tools SaaS environment.</li><li>Ability to use AI tools to accelerate customer-facing work: researching prospect environments, generating tailored demo code, building proof-of-concept repos etc.</li><li>Ability to be autonomous and self-motivated in a remote-first work environment, while you also enjoy getting to know your colleagues and helping others.</li><li>Exceptional empathy and curiosity. You love working with customers and take pride in seeing them succeed.</li><li>Proactive and ownership-oriented mindset to help build long-lasting partnerships with Checkly’s customers.</li><li>Excellent spoken and written English skills.</li><li>Located in the US (ET or CT time zones).</li></ul><h2>Why us?</h2><ul style="min-height:1.5em"><li>Transparent salary. (more info below)</li><li>Become part of a fast-growing, and international team where your work matters—your impact won’t get lost in layers of bureaucracy.</li><li>Stock options</li><li>Flexible paid vacation + your local public holidays</li><li>Paid sick leave & up to 14 weeks of paid parental leave</li><li>$1,500 learning, visiting and wellbeing budget</li><li>Annual company on-site</li></ul>Find out more <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.notion.so/Benefits-Perks-ad474bec3a5d4d17bfbb43ebae3fec9c?pvs=21">here</a>.<h2>What we pay</h2>Fair, competitive, and transparent pay is very important for us. Therefore we work with a <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.notion.so/f3c42feab82b444a9cbf8fed545cb727?pvs=21">standardized salary calculator</a> that includes several factors such as seniority level as well as location.For this role, the range is<ul style="min-height:1.5em"><li>$179k-208k OTE (70% base + 30% commission) for someone in the US</li><li>$224k-$260k OTE (70% base + 30% commission) for someone in US Tier 1 locations like NYC, Boston</li></ul><h2>Apply</h2>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 <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.notion.so/Checkly-Hiring-Playbook-54bc05178d3b4118a15effe885f96d1a?pvs=21">hiring playbook</a> and open-sourced our <a target="_blank" rel="noopener noreferrer nofollow" href="https://www.notion.so/Checkly-s-Employee-Handbook-f262e36a64d641af8588a1c09bc0ff48?pvs=21">employee handbook</a>. There you'll find a sneak peek of who we are, how we work and what you can expect in our hiring process.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...