Mid-Market Account Executive

Mid-Market Account Executive

Featured Boston, MA April 6, 2026

Job Description

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.

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 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.

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.

Responsibilities:

• Drive the entire sales process, including self-sourced prospecting, discovery, tailored demonstrations, and complex negotiations.
• Develop and execute targeted account strategies for mid-market and strategic prospects, leveraging your experience to quickly identify and engage the right stakeholders
• Lead complex, multi-threaded deals with economic buyers, legal teams, and executives — bringing credibility and executive presence to every conversation
• Serve as a trusted advisor to prospects by deeply understanding their contracting and business challenges and positioning LinkSquares as the strategic solution
• Collaborate cross-functionally with Sales Engineering, Customer Success, and marketing to drive deals forward and ensure a seamless customer experience
• Maintain high data integrity and transparent forecasting within Salesforce and Gong to contribute to the team's collective success
• Contribute to a culture of continuous improvement — sharing competitive intelligence, deal learnings, and best practices with the broader team

Requirements:

• Proven ability to manage the full sales cycle in a B2B SaaS environment, specifically managing deals with an ASP of $50k+.
• Demonstrated ability to self-source pipeline, you have a "playbook" for prospecting and don't rely solely on inbound traffic.
• Experience navigating deals with multiple stakeholders (Legal, IT, and Finance) is highly preferred.
• Proficiency with Salesforce, Gong, LinkedIn Sales Navigator, and ZoomInfo
• Strong executive presence and the ability to lead high-stakes conversations with confidence and credibility
• You are resourceful and solution-oriented, focusing on how to overcome hurdles rather than why they exist
• Team-first mentality with the maturity to operate independently and contribute to the broader organization

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.

Company Details

LinkSquares

Industries: AI Native, Enterprise Software / SaaS

Location: Boston, MA

Job Function: Sales & Business Development