Senior Sales Engineer (USA)

Senior Sales Engineer (North America)

United states (Remote) | Full-time permanent

The Company

Checkbox is a Sequoia-backed technology start-up with a mission to enable meaningful work for all. To achieve this, we built a no-code automation platform with the belief that the power of digital creation needs to be accessible to everyone, not just IT teams. Seeing non-technical users surprisingly delighted when they use our technology to create in ways they never thought they ever could motivate us. Whilst our mission is big, our focus is sharp. Our customers today are primarily in-house legal departments from companies including SAP, BMW, Allianz, Pinterest, and Coca-Cola.

Recently, we expanded our offering to not only help people do meaningful work, but manage it too. This came with the launch of our AI-powered Matter Management product – the “JIRA for lawyers”. This is part of our broader vision to be the “Legal Service Hub” for organizations, responsible for how legal work is raised, allocated, managed, and resolved. We believe that one day the Legal Service Hub will be as ubiquitous for legal teams as the CRM for commercial teams and we believe that Checkbox will be the market leader for this.

As a company, we are an energetic and tight-knit team of about 70 people across the United States, Australia, and Asia, made up of incredible high performers and Co-Founders in the Forbes 30 Under 30 list. Our culture is one of our superpowers. It's what people talk about when they join us, work with us, and leave us. Read about what makes all of us a "Checkmate" here: https://www.checkbox.ai/core-values.

The Position

At Checkbox, we pride ourselves on a simply first-class pre- and post-sale experience. It is one of the things we’re known for, what we celebrate internally, and a key driver for our overall success as a company. Customers are our lifeblood and why we do what we do, so we hold a very high standard when it comes to ensuring that Checkbox customers always feel like they have not only partnered with the best technology, but the best team in the industry.

As a Senior Sales Engineer, you will be partnering closely with the Account Executives in our Sales team to close enterprise deals. Your role in the sales process is to help our largest and most complex prospects realise the value and fit of the Checkbox platform to their needs at a technical level. This is a very important role because whilst the Checkbox product is easy to use and powerful, it is your role that allows the prospective customer to conceptualise that value in their context. This role requires a deep understanding of our prospective customers’ needs, strategic planning capabilities, and the ability to deliver complex solutions in a way that is easy to understand while being able to adapt and pivot to meet their needs. You will also play a key role in mentoring junior team members and driving demo and delivery strategies across the organization. This role is highly technical – we are looking for someone with a desire for deep product knowledge, and the confidence to leverage that knowledge to add value to prospects!  

Although we work with some of the largest companies in the world, our company culture is anything but corporate. Ambitious people that want to collaborate on interesting challenges and find joy out of working with talented, passionate people will thrive here!

In this position, you will:

• Report directly to the Director of Sales Engineering and partner closely with Account Executives, Sales Leadership, and cross-functional teams

• Support Account Executives on addressing more complex product, technical and integration questions.

• Support Account Executives by addressing how Checkbox differentiates from or works with existing, common enterprise systems.

• Own the technical strategy for complex, high-value enterprise opportunities, partnering with Account Executives to drive deal progression and successful closes.

• Strategize with Account Executives on the sales strategy and plan for each account

• Collaborate with the sales team in pre-sale trials, proof-of-concepts, workshops, and business case development to ensure a seamless transition from sales to customer success. Provide technical expertise and strategic input to support the sales process.

• Lead technical discovery calls with prospects to understand their desired user journey and functional product and integration requirements.

• Scope, design, build, and demo legal workflows for prospects on the Checkbox no-code platform, helping them ideate and visualize what a partnership with Checkbox will help them unlock.

• Develop and maintain strong relationships with key prospect stakeholders.

• Be responsible for providing responses during the sales process to technical documentation relating to information security, product capability, and enterprise architecture.

• Lead hands-on product workshops with prospects and customers to build applications live on the Checkbox product.

• Deliver higher complexity product demonstrations to prospects.

In addition, you will:

• Contribute to the development of sales engineering best practices, enablement materials, and repeatable technical sales processes.

• Mentor and support junior SEs, sharing best practices, providing guidance, and helping to elevate the overall performance of the sales engineering team.

• Act as a key liaison between Sales, Product, Engineering, and Customer Success to ensure alignment from pre-sales through implementation.

• Be the technical voice of our prospects, helping address escalated product issues with speed and urgency, orchestrating and rallying resources within the company as needed.

• Provide ongoing competitive and market insights to Sales and Product leadership to refine positioning and go-to-market strategy.

• Maintain the suite of standard 'kitbag' product demonstrations used by Account Executives.

• Support team and organizational needs through additional assigned duties.

About you

• 5+ years of experience in technical, customer-facing roles within SaaS, with a strong emphasis on sales skills including discovery, value-based selling, objection handling, and executive-facing presentations.  

• You are in LegalTech or legal operations, and/or you have experience with lawyers, law firms, and/or in-house legal departments.

• Proficient in having conversations with IT stakeholders and addressing common concerns around interoperability and differentiation from common enterprise systems including ServiceNOW, Jira, Microsoft Power Platform (Power Automate, Power Apps, SharePoint, Power BI), Salesforce, etc.

• Proficient with JavaScript and developing system integrations using REST APIs with enterprise ERP, CRM, DMS and other systems.

• You have strong technical acumen, with experience configuring software platforms, managing technical projects, and developing integrations.

• You are creative, driven, and have strategic vision to help our prospects see a better future with Checkbox.

• You are high-energy, improvisational, and an excellent communicator, which you pair with a strong attention-to-detail and an appreciation for the importance of the user experience.  

• You are willing to consistently go beyond the call of duty for the team, and to challenge the status quo to help Checkbox be better.

• You have proven to thrive in an entrepreneurial environment that absorbs rapid change and disruption.

• You are outcome-oriented, adaptable, collaborative, memorable and personable.

• You take ultimate ownership over the success of your prospects and make every decision with an eye towards prospect experience and satisfaction.

Compensation & Benefits

• Competitive salary & equity – We believe in employee ownership and comfortable compensation for our employees so that they can be as happy and productive as possible without any reservations.

• Insurance coverage – We cover your health insurance, including dental and vision.

• 401K savings – We match contributions to your 401K retirement savings.

• Generous and flexible leave – We provide 20 days paid leave a year (paid as cash if unused) and parental leave (including secondary carer), with a culture of approving and encouraging time off as needed.

• Remote working arrangements – Our US team is distributed across the country, meaning you can work from wherever you’d like provided it is within the country.

• Personal learning & development budget - Continuous development and growth (#suckless) is one of our core values, and we believe in investing in our own home-grown leaders.

• Expense policy – You can expense small work-related items and salary sacrifice larger items within reason.

• Company-wide social events – We have some wicked annual off-sites (past events include a massive boat party, a few days stay in a mansion in Australia’s wine region, and a week in Bali!)

• Transparent & open culture - Enjoy the benefits of an open culture where all questions and feedback are welcomed so we can be a better company day by day.

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