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SessionM, Inc.

Director of Sales Enablement

– Boston, Massachusetts
Employment Type Full Time
Minimum Experience Manager/Supervisor


SessionM is looking for a Director of Sales Enablement to transform our sales enablement programs and support ongoing training.  This role is a unique opportunity to develop a well-rounded comprehensive sales onboarding and certification program and drive impact from day one.


  • Develop and implement a comprehensive and sustainable training and development process to support the transformation of the sales organization
  • Establish key performance indicators to track sales training program efficacy
  • Creation of world-class curriculum for product certification in co-ownership with product marketing and sales 
  • Manage the sales enablement content repository in conjunction with marketing to ensure all information is easily and readily accessible at point of need
  • Design and implement comprehensive initial onboarding and ongoing training programs with a 30-60-90 day plan for sales team members at all levels
  • Act as a liaison between Sales, Customer Success, Marketing, and Product teams to craft sales playbooks, training decks, demo trainings, competitive intel, prospect overviews, etc.
  • Ensure sales is prepared to effectively sell against the competition, including partnering with our competitive intelligence resources
  • Stay informed on cutting-edge tools and technology that may be leveraged to improve sales productivity
  • Work with key strategic partners on go to market strategy and messaging
  • Influence key sales events including Annual Sales Kick Off and Sales Leadership events
  • Field ad hoc content and support requests from sales team
  • Determine content adoption metrics and define sales enablement best practices
  • Identify the right third party vendors to fill sales skill competency gaps as needed


  • 7+ years experience in sales enablement with a proven track record of success
  • Ability to work under pressure, highly adaptable and well organized
  • Proven track record in creating, delivering, and training successfully with measurable results in fast paced environments
  • Strong, detailed knowledge of software sales cycles and operations
  • Strong ability to represent concepts, as well as summarize and communicate complex ideas into curriculum with a sense of how sales professionals think, operate and absorb training
  • Extensive experience supporting sales organizations, processes, and strategy
  • Hands-on experience with LMS tools and processes (Learncore, SFDC, etc.)
  • Experience in a high growth, startup environment.
  • Experience in curriculum development, training, and delivery.
  • Ability to thrive in a fast-paced, unpredictable environment.
  • Adept at project management and cross-functional collaboration.

Compensation & Benefits

  • Competitive compensation based on experience level
  • Healthcare HMO & PPO 
  • Stock options and 401k
  • Flexible Spending Accounts
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  • Location
    Boston, Massachusetts
  • Employment Type
    Full Time
  • Minimum Experience
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