Enterprise Account Executive; remote, ET, CT or MT

Enterprise Account Executive (remote, ET, CT or MT)

Join Checkly as an Enterprise Account Executive (remote, ET, CT or MT) to 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. Our platform is trusted by teams at 1

Password, Crowd Strike, Render, Linked In, and Vercel, and we recently raised $20 M in Series B funding from Balderton, CRV, and Accel.

As a member 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. If you thrive in an entrepreneurial environment and love closing deals that genuinely help developers, this is the place for you.

• 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 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.

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 culture.
• Fast‑growing international team where your impact matters.
• 27 days of paid vacation plus 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.

Fair, competitive, and transparent pay is very important for us. For this role, the range is $255K – $300K OTE (50% base + 50% commission).

If this sounds interesting, please apply! We encourage diverse candidates to apply, even if you feel you meet only part of the requirements.

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.