Sales Enablement Specialist

On Site Full TimeBoston, MA, United StatesLinkSquares

LinkSquares is a fast-growing LegalTech software company, rated as one of “The Best Places to Work in 2022” by the Boston Business Journal and BuiltIn Boston. We’ve built an end-to-end AI-powered Contract Lifecycle Management (CLM) SaaS product suite used by some of the world’s most prominent companies (Fitbit, Igloo, DraftKings, Cogito, and even the Boston Celtics).

Contracts are the lifeblood of business and power everything from revenue, obligations, financing activities, and reporting. At LinkSquares, our product takes the manual, time-consuming, tedious tasks out of the contracting process. With LinkSquares, legal teams save time, cut costs, and improve business outcomes. We are a 400 + person company headquartered in downtown Boston.

The Sales Enablement Specialist role is responsible for building and overseeing the SDR training program and related data & materials.


  • Create, implement and deliver training programs focused on a sales methodology to improve the performance of our SDR team
  • Develop training materials and resources, including presentations, handouts, exercises, and assessments, that support the training program and can be used for ongoing learning and development
  • Perform hands-on mentoring of new hires for sales systems, prospecting, and cold calling
  • Own Sales Tools trainings, adoption, troubleshooting, and QBR reviews
  • Design and develop training programs focused on sales techniques (“Outcome Selling”), product knowledge, and customer engagement to improve the performance of the sales team


  • Mastery in sales tools (Outreach, LinkedIn Sales Nav, Zoominfo, Crunchbase), outbound metrics, and outbound conversion metrics (the Science)
  • Be proficient in cold-call strategy and scripts
  • Be an expert in coaching, training and managing SDR teams
  • B2B software experience required
  • Be a self-starter, who learns quickly and adapts to change; can make recommendations and assume responsibility quickly
  • Video prospecting experience a plus

About LinkSquares

Founded in 2015 with headquarters in Boston, we offer a comprehensive and competitive benefits package that includes medical, dental and vision plans for employees and their families, health and wellness programs, a 401(k) plan, unlimited vacation, paid parental leave and more. Learn more here:

For legal teams needing to move their business forward faster, LinkSquares provides a contracting platform for writing better contracts, analyzing what’s in existing contracts, and working better with their team. It differs from other tools on the market with its powerful AI insights, speed to providing tangible results, and ability to help the entire company collaborate better. LinkSquares saves companies hundreds of hours and thousands of dollars by eliminating manual contract processes and reducing the need for outside counsel. For more information, visit

LinkSquares is an Equal Opportunity Employer and does not discriminate on the basis of an individual’s sex, age, race, color, creed, national origin, alienage, religion, marital status, pregnancy, sexual orientation or affectional preference, gender identity and expression, disability, genetic trait or predisposition, carrier status, citizenship, veteran or military status and other personal characteristics protected by law. All applications will receive consideration for employment without regard to legally protected characteristics.

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