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Sales Director, Coaching and Development

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 offices in Washington DC, and Pittsburgh, PA.

Job Summary


Calling all sales coaches, process improvers, team builders, and mentors. We have an exceptional opportunity to bring your knowledge, past sales experience, and passion to our team. We seek someone willing to get into the weeds, help our junior sales team hit their goals, coach them to be stronger closers and create an environment of support not competition. If sales, but more importantly personal development, is your passion, then we have an awesome role for you here. 


Develops and implements sales strategy within the mid-market to achieve corporate growth goals. Manages and leads a group of sales representatives and account managers responsible for selling Skyword's solutions to new companies and business units within existing customers, along with retaining existing business. Responsible for hiring and maintaining a world class team, including coaching and building individualized skills development plans for each member of the team. Ensure the team’s approach and customer facing activity aligns with company values (i.e. putting the customer first). Provide day to day management of the team to ensure customers receive what they need and to meet revenue targets. Clients facing- including joining team members on customers calls and meetings, overseeing proposal development, and presenting proposals to clients.

Primary Duties and Responsibilities

  • Responsible for new logo, upsell, and renewal sales in the mid-market

  • Talent Development- coaching and skills improvement for each member of the team

  • Building the team- recruiting, interviewing, hiring and promoting

  • Pipeline management- ensure adequate pipeline coverage to achieve revenue targets

  • Efficiency- manage the team to maximize revenue per account

  • Customer meetings- meets with key clients, assisting sales representative with maintaining relationships and negotiating and closing deals.

  • Predictability- Future revenue forecasting 

  • Represents Skyword at trade meetings and conferences

  • Coordinates with other departments, including marketing, pre-sales (sales support), sales development, and professional services

  • Create trainings, playbooks, and other sales materials to support the team


  1. Communication Proficiency.

  2. Results Driven.

  3. Initiative.

  4. Customer/Client Focus.

  5. Coaching and skills development

  6. Performance Management.

  7. Leadership.

  8. Business Acumen.


Work Environment

This job operates in a professional office environment. This role routinely uses standard office equipment such as computers, phones, photocopiers, filing cabinets and fax machines.


This position requires up to 50% travel. 

Required Education and Experience

  1. Bachelor’s degree.

  2. 5+ years in sales.

  3. 3+ years in a management position leading a large staff of employees.

  4. Broad knowledge of the field with demonstrated leadership skills.

  5. Demonstrable track record of meeting or exceeding revenue targets in complex sales environments

  6. Demonstrable ability to communicate, present and influence key stakeholders at all levels of a client organization

  7. Experience developing strong interdepartmental relationships with colleagues to facilitate a strategic approach to clients and successful delivery of solutions  

  8. Proven ability to present and explain the technical elements of products or services

  9. Proven ability to retain and grow multiple accounts, while maintaining sharp attention to detail

  10. Knowledge of current marketing trends, technologies and best practices

  11. A deep-seeded curiosity and openness to learning new things

  12. Knowledge and familiarity with Salesforce 


Compensation and Benefits:

Competitive salary; medical; dental, life, and disability insurance plans; three weeks paid vacation; 11 paid holidays, and an open, friendly working environment.

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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