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Sales Director

Skyword is seeking a seasoned sales director that has a demonstrated history of consultative sales. This is a revenue-driving role with an aggressive monthly quota. The ideal candidate can effectively build and manage client relationships with senior level marketing executives at Fortune 1000 companies. This person will be responsible for creating a target account list, securing client meetings, facilitating client workshops, building a sales strategy for a content marketing program, securing the business and transitioning the account to the services team.

The ideal candidate is aggressive and has a passion for solving client’s business challenges by providing thought leadership. Successful candidates have an ability to engage prospects and build rapport quickly; they thrive on creative thinking and creating custom solutions; and they are able to effectively manage a short sales cycle.

The position will report to the Executive Vice President.


  • Understand client challenges and manage through overcoming objections by identifying creative subscription-based solutions.
  • Ability to research, build and deliver a thoughtful content marketing strategy approach.
  • Create sales prospecting strategies that may include email campaigns, cold calling, or publishing industry relevant content/articles.
  • Not afraid to challenge conventional thinking and offer an alternative approach.
  • Achieve monthly, quarterly and annual revenue goals by developing and managing opportunities.
  • Provide accurate monthly sales forecasting.
  • Enter all opportunity information into
  • Create and manage contract process through signature.
  • Work with finance team and clients to coordinate signature process of Master Services Agreements (MSAs).
  • Build and deliver presentations to represent client solutions.
  • Focus sales efforts by identifying target accounts to prospect into.  
  • Keep management frequently informed by submitting activity progress, sales strategy and path to signature.
  • Successfully transition new business opportunities to services team.
  • Find opportunities to build pipeline via attending industry events or participating in professional networking groups.
  • Participate in CMO industry events by selecting and facilitating one-on-one meetings with senior level marketing professionals.
  • Activate network through social selling via LinkedIn or Twitter.


  • Position is based in Boston office but open to remote position for the right candidate
  • 15+ years of b2b consultative experience desired
  • Hunter mentality
  • Ability to work independently
  • SaaS experience preferred
  • Self-starter with an ability to deliver on targets without constant supervision
  • High-caliber work ethic and preparation, with focused attention to detail
  • Proficiency with Microsoft Office
  • Experience with is preferred
  • Excellent written and verbal communication skills are essential
  • Must be a good communicator and skilled at developing relationships
  • Ability to thrive in a fast-paced environment
  • Skilled at prioritizing and managing pipeline effectively
  • BA/BS required
  • 30% travel is required

Compensation & Benefits:
Competitive market-based salary with rich commission and bonus incentives. Benefits include medical, dental, life, 401k and disability insurance plans; three weeks paid vacation; 11 paid holidays and an open, friendly work environment.

About Skyword:

Skyword moves brands – and their content – forward. By embracing a sustainable, scalable approach to original storytelling, Skyword liberates brands from ineffective marketing practices and inspires them to create deeper connections with their customers. With a powerful combination of enterprise-class technology, authentic voices, and professional services, Skyword propels clients’ content marketing programs to new levels of excellence. Skyword is a privately held company headquartered in Boston, MA, with an office in Pittsburgh, PA.

Skyword is an equal opportunity employer and considers qualified applicants for employment without regard to race, color, creed, religion, national origin, sex, sexual orientation, gender identity and expression, age, disability, veteran status, or any other protected factor.

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