Mid-Market Account Executive

LinkSquares • Boston, MA

1d • $75,000 - $115,000

About The Position

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.

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

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

Benefits

• medical
• dental
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed