Enterprise Account Executive; remote, ET, CT or MT

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

Apply for the Enterprise Account Executive (remote, ET, CT or MT) role at Checkly
.

$255,000 – $300,000 per year (50% base + 50% commission)

Remote with optional NYC office. Checkly is a Series B Dev Tools SaaS company.

You will report directly to Tony, VP of Sales, and focus on enterprise accounts that include:

• Account expansion within our strong install base
• Warm inbound leads from our growing market presence
• Net‑new logo hunting

This role is about solving real problems for engineering teams through testing, monitoring, and observability.

• 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 with strong prospecting and lead‑nurturing skills.

• Comfortable talking shop with CTOs, VPs of Engineering, and developer teams.
• Interested in modern web technologies.
• Can translate technical value into business impact.

• 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.

• 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 required. Optional access to NYC office.

• Transparent salary model.
• Stock options.
• Flexible work hours, async‑first culture, and transparent communication.
• Fast‑growing, international team with high impact.
• 27 days of paid vacation plus local public holidays.
• Paid sick leave and up to 14 weeks of paid parental leave.
• $1,500 annual learning, visiting, and wellness budget.
• Bi‑annual company retreats.

Fair, competitive, and transparent pay is important to us. The range for this role is $255k – $300k OTE (50% base + 50% commission).

If this sounds interesting, please apply! We value transparency and want to hear what you bring to the table.

Mid‑Senior level.

Full‑time.

Sales and Business Development.

Technology, Information and Internet.