Enterprise Account Executive (remote, USA)

(Remote with option to go to NYC office if convenient, ET, CT or MT, Series B DevTools SaaS)

Join Checkly as a Senior Account Executive and empower developers to own and ensure application performance and reliability - from pull request to post-mortem!

Checkly helps engineers build reliable products by unifying testing, 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 1Password, CrowdStrike, Render, LinkedIn and Vercel, but we’re just getting started. 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. 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 flexible and async-first startup environment with inclusive benefits and full transparency about how we pay.

We're looking for a Senior Account Executive to join our sales team of driven Account Execs and savvy Solution Engineers. You will report directly to Tony, our VP of Sales. You’ll focus on enterprise accounts with a mix of:

• Account expansion within our strong install base

• Warm inbound leads from our growing market presence

• Net-new logo hunting

This isn’t about pushing software. It’s about solving real problems for engineering teams who live and breathe code quality.

Has the track record

• Consistently crushes SaaS sales targets and knows the enterprise cycle inside-out.

• Has experience and enjoys growing accounts AND landing new logos.

• Previously worked as an SDR and has strong prospecting/lead nurturing skills.

Gets the technical side

• Comfortable talking shop with CTOs, VPs of Engineering, and developer teams.

• Interested in modern web technologies.

• Can translate technical value into business impact.

Thrives in our environment

• Loves the energy and autonomy of a remote-first startup

• Enjoys collaborative problem-solving with Solution Engineers and the broader team

• Ready to travel frequently across the US to build face-to-face relationships

Communicates like a pro

• Exceptional written and verbal English skills

• Confident presenting to C-suite executives and technical teams alike

• Can adapt communication style from boardroom to Slack channel

Location: US East, Central or Mountain Time is required. Optional access to our NYC office.

• Transparent salary (more info below).

• Stock options.

• Flexible work hours, async-first (low meeting, high productivity) and transparent culture.

• Become part of a fast-growing, and international team where your work matters. Your impact won’t get lost in layers of bureaucracy.

• 27 days of paid vacation + your local public holidays.

• Paid sick leave & up to 14 weeks of paid parental leave.

• $1,500 learning, visiting and wellness budget.

• Bi-annual company retreats.

Find out more here.

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, the range is $270k - $300k OTE (50% base + 50% commission)

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.