Outbound Sales Development Representative (US)

Full-time / Permanent / United States (Remote)

The Company

Checkbox is a Sequoia-backed technology start-up with a mission to empower anyone to build software. This is important to us because with our rapidly digitising world, we believe the power of digital creation needs to be accessible to everyone, not just IT teams. Seeing non-technical users surprisingly delighted when they are able to create in ways they never thought they ever could using our technology, motivates us. Across the enterprise, users use drag and drop to build their own solutions that automate manual workflows, analysis, and document creation. Since launching the product at the beginning of 2019, we have signed on big brands like Deloitte, Telstra, Allianz and Coca-Cola, winning 14 awards globally. As a team, we have incredible talent that have previously led global SaaS success stories and Co-Founders in the Forbes 30 Under 30 list. As people, we are high performers who are positive, collaborative, open and direct in our communication, and care a lot about this business and each other.

The Position

We are looking for someone who is passionate about engaging directly with potential customers and helping them uncover their problems. The Sales Development Representative at Checkbox is responsible for prospecting and cold outreach to those prospects via primarily phone calls and emails. You will be working closely with a Checkbox Account Executive and will be responsible for laying the foundation for the opportunity by engaging with prospects and customers, helping them understand the value of Checkbox, and moving them forward in the sales process. As Checkbox’s first point of contact with a prospect, you play a key role in building the Checkbox brand, creating a great first impression, and building momentum for not only the sales team but the company as a whole.

In this position, you will:
+ Create and prioritize strategic target account lists with Account Executives
+ Generate new business pipeline for Account Executives through email, cold calling, event follow-up, social etc.
+ Provide a great experience for Checkbox’s prospective customers
+ Maintain an up-to-date knowledge of our product and its value to customers
+ Demonstrate an ability to understand prospect pain points and attract new customers
+ Work with other functions to improve business processes
+ Engage in team development and mentoring


+ You are resilient and able to overcome objections
+ You are diligent with process, professional and have strong written and verbal communication
+ You are an active listener and adaptable in conversation
+ You have a fun, positive and collaborative attitude towards work and love to take ownership of everything you do


+ Competitive winning attitude, but with an ability to be coachable
+ Experience working at a high growth SaaS software start-up company
+ Legal education background or previous career as a lawyer


+ Remote working arrangements
+ Health, vision and dental insurance paid for by company
+ 4 weeks of paid leave

Compensation will vary based on experience but will consist of salary and commission.

Want to jump on board?

If you find this exciting and think you have what it takes, we would love to meet you. Please contact us at careers@checkbox.ai with your CV.

Daniil Ivanov, Tech Lead

“At Checkbox, you are surrounded by intelligent, driven people who are passionate about what they do. There is always an opportunity for personal and professional growth, and to try new technologies.”

– Daniil Ivanov, Tech Lead

Aditi Dalal, Customer Success Manager

“Working at Checkbox is a chance to choose your own adventure. Each day presents a new opportunity to work with and learn from a dedicated and close-knit team to shape the future of a fast-growing startup.”

– Aditi Dalal, Customer Success Manager

Learn About Our Values

At Checkbox, we’ve created an amazing and high performing culture for our people. Learn more about the values that define who we are.