Senior Account Executive (Director of LegalTech Sales) - North America

Full-time / Permanent / North America (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

This role involves working with in-house legal teams to understand their challenges and aligning value from the Checkbox no code workflow automation software to result in license sales. As part of a scaling start-up, you are expected to be a resourceful, independent hunter who is able to effectively qualify and close new opportunities without the backing of a universally known brand or robust sales infrastructure. You will work closely with a Sales Development Representative (SDR) and will be supported by a Pre-Sales Engineer and the Marketing team. You need to be able to confidently and successfully lead, navigate and close a complex sales process involving stakeholders at all levels of the enterprise. The right person for the role will be able to build strong relationships and constructively challenge the thinking of senior decision-makers and champions within legal teams such as the Chief Legal Officer, General Counsel, Head of Legal Operations, as well as stakeholders in IT and procurement.

As one of our first ever North America team members, you’ll be given the exciting opportunity to build and contribute to the organization’s go-to-market strategy, culture and success, and will be working closely with the CEO to do so.

In this position, you will:
+ Deliver against quota (license revenue only) with a strong emphasis on new business sales to in-house legal teams
+ Work with your SDR to convert meetings booked into opportunities and new license revenue
+ Forecast, manage, execute & report on your sales plan
+ Log and maintain accurate and detailed reporting and notes on sales activity and opportunities in the CRM


The ideal candidate would exhibit the following:


+ At least 5+ years of experience selling SaaS technology to enterprise companies
+ Proven track record of delivering consistently or exceeding sales quotas
+ Strong experience in consultative, enterprise solution sales
+ Comfortable with objection handling enterprise IT, procurement, and budget objections
+ Have worked as an SDR or worked directly with SDRs
+ Sharp, quick & adaptable learner who is results driven and is a consistent high achiever
+ Able to work resourcefully and independently to deliver results


+ Experience selling software to in-house legal teams
+ Experience selling automation or workflow or low/no code technology
+ Existing network of leads in the corporate in-house legal space
+ Has a 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 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.