Commercial Account Executive

About the company:

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 linksquares.com.

About the team:

Join a high-velocity, collaborative sales 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.

About the role:

We are looking for an Account Executive who is energized by a fast-paced environment and eager to master the art of full-cycle sales. In this role, you aren’t just following a script; you are a disciplined professional who can balance high-volume outreach with strategic deal management. You will own the entire sales process—from initial research and prospecting to engagement and closing new business.

Responsibilities: 

• Proactively identify and engage new business opportunities through a mix of creative research, personalized emailing, and persistent outbound outreach.
• Lead prospects through the entire journey, including discovery, product demonstrations, proof-of-concept trials, and final negotiations.
• Translate the power of AI into clear business value for SMB leaders, helping them see how LinkSquares can transform their daily operations.
• Manage your pipeline with rigor, utilizing Salesforce and Gong to accurately forecast and prioritize your daily activity against key performance indicators (KPIs).
• Actively participate in team coaching and training sessions to refine your sales craft and stay ahead of legal tech trends.

Requirements:

• Proven experience in a full-cycle sales role (managing a deal from lead generation through to close).
• Previous experience in B2B software sales is a plus, particularly with deals in the $20k–$40k range.
• You take initiative and are comfortable building your own book of business through consistent outreach and follow-up.
• Adaptability: The ability to move quickly between different tasks—from a cold call to a high-level demo—without losing momentum.
• Familiarity with Salesforce, Gong, LinkedIn Sales Navigator, or ZoomInfo is highly preferred.

Note on Requirements: At LinkSquares, we value diversity of experience. If you meet the majority of these requirements and have a passion for transforming the legal-tech landscape, we encourage you to apply. We are looking for the right person, not just the right resume.

Compensation for this role includes an annual base salary between $75,000 to $115,000. On-target earnings range between $150,000 to $230,000, split 50/50 between base salary and commission. Total compensation can be higher for those who exceed targets. LinkSquares takes into consideration a number of factors when determining an employee’s starting salary, including work location, job-related skills, and relevant education, experience and training. The recruiter assigned to this role will share more information about the specific compensation and benefit details associated with this role during the hiring process. 

Candidates are eligible to participate in the company’s benefit programs. LinkSquares’ benefits include but are not limited to medical, dental, and vision insurance, 401k retirement plan with a company match, equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure), flexible paid time off, generous parental leave, life and disability insurances and more.

LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.