Mid-Market Account Executive

<p><strong>About the company:</strong></p> <p>LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit <a href="http://linksquares.com">linksquares.com</a>.</p> <p><strong>About the team:</strong></p> <p>Join a high-velocity, collaborative<strong> </strong>sales<strong> </strong>organization that sits at the intersection of AI innovation and legal technology. Our Sales team goes beyond quarterly financial goals, instead serving as strategic partners to our customers. We are consultants helping modern businesses, like TIME and Peregrine Hospitality, solve complex contracting bottlenecks and advance contract innovation. We prioritize a "learn and get better" mentality, balancing strategic, high-value deals with fast-moving transactional opportunities in a supportive, team-first environment.</p> <p><strong>About the role:</strong></p> <p>We are looking for an <strong>Account Executive </strong>who brings proven mid-market sales experience and the drive to keep building something great. You have a proven track record, you know how to run a sophisticated sales cycle, navigate complex organizations, and close meaningful deals. But you’re not coasting. You’re still hungry, still willing to pick up the phone, still energized by the challenge of opening new doors and winning competitive deals.</p> <p>This is a full-cycle role. You will own your pipeline from prospecting through close, which means you’ll need to be comfortable generating your own opportunities, not just working inbound. You know how to get creative when the pipeline needs attention and you don’t wait around for leads to come to you.</p> <p><strong>Responsibilities:</strong></p> <ul> <li>Drive the entire sales process, including self-sourced prospecting, discovery, tailored demonstrations, and complex negotiations.</li> <li>Develop and execute targeted account strategies for mid-market and strategic prospects, leveraging your experience to quickly identify and engage the right stakeholders</li> <li>Lead complex, multi-threaded deals with economic buyers, legal teams, and executives — bringing credibility and executive presence to every conversation</li> <li>Serve as a trusted advisor to prospects by deeply understanding their contracting and business challenges and positioning LinkSquares as the strategic solution</li> <li>Collaborate cross-functionally with Sales Engineering, Customer Success, and marketing to drive deals forward and ensure a seamless customer experience</li> <li>