Commercial Account Executive (Boston, remote)

(Remote in Boston with regular travel to the NYC office, Series B DevTools SaaS)

Join Checkly as a Commercial 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.

What you'll do

We're looking for a Commercial Account Executive to join our sales team of driven Account Execs and savvy Solution Engineers. You will directly report to Tony, our VP of Sales. You’ll focus on commercial 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 fro engineering teams who live and breathe code quality.

What you should have

• You know the SaaS sales cycle end-to-end.

• You have worked in a similar position before and showed excellent performance closing new contracts as well as growing a customer and making them successful.

• You are interested in current web technologies and feel comfortable speaking with technical buyers and developers.

• You worked as an SDR before or have similar experience and know how to nurture leads and break into accounts.

• You enjoy hunting new logos and know how to generate pipeline

• You feel comfortable working in a team where everyone helps each other out.

• Familiarity working with a remote-first company.

• Excellent spoken and written English skills. You are a strong communicator, in presentations, calls, and emails.

• We believe it is important to meet with our customers in person which will require that you will be traveling frequently across the USA.

• Boston is a hard requirement for this role.

What we offer

• Transparent salary (more info below).

• Stock options

• Become part of a fast-growing, international, and remote-first team where you can have a real impact

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

• 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 wellbeing budget

• Bi-annual company retreats

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, the range is $216k - $240k OTE (50% base + 50% commission).

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.