Join a leader in the industry.

Director of Sales


We are looking for a seasoned Director of Sales to manage our team of business development executives and account managers to grow new business and establish long term relationships with new clients in our niche technology sector.

Specific duties include:

  • Sales Team Management – Guide the Sales team to focus on activities that will lead to exceeding sales goals through a regular cadence of meetings, individual one-on-ones, strategic account planning, pipeline reviews and opportunity strategy.
  • Sales Opportunity Support - Support the Business Development Executives and Account Managers as they generate leads, work to close sales opportunities, and foster long-term consultative relationships with clients.
  • Training and Development - Assess sales and Account Management team strengths and weaknesses and implement training and individual improvement plans as required.
  • Recruiting new team members - Maintain sales recruiting efforts to ensure the team continues to operate at high levels as we grow and expand.
  • Business Development - Work with the sales team to identify and develop new markets and partners.
  • Account Management - Meet regularly with clients to develop strong relationships and assess the quality of their relationship with Chesapeake.
  • Reporting - Develop sales performance reporting metrics and use information to development insights on team and individual performance.
  • Commission Management - Work with CEO and CFO on confirming commissions and resolving any issues that might arise in the course of a year.
  • Recognition - Develop and implement sales team recognition program.
  • Internal Process Development - Leader will work with sales operations, Solutions Architects and service delivery on ensuring a high degree of efficiency. This will include quarterly review and collaboration with each department to address growth pains as Chesapeake continues to grow, and legacy processes require modification.
  • Vendor Management - Work with CEO on vendor relationship management elements such as Chesapeake purchase and corresponding sales goal(s), vendor incentives, vendor co- selling and co-marketing.


Chesapeake Systems provides a competitive salary range and a full range of benefits. We are a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, national origin, age, sex, religion, disability, sexual orientation, marital status, military or veteran status, gender identity or expression, or any other basis protected by local, state or federal law.

Qualifications & Skills

What you need to be successful

  • Strong track record of success in selling complex technology solutions to large companies.
  • Quantifiable results in delivering overall sales targets for company.
  • Background in selling to companies in the broadcast, media production, and digital media industries. Candidates that have worked with companies that generate large quantities of rich media content are a great fit to work with our experts.
  • Ability to work with software partners on an integrated sales process.
  • A passion for working with clients to identify and solve their most challenging technology problems. Must be a natural networker and someone who loves to build strong relationships.
  • Experience in establishing best practices in sales teams working with Solutions Architects, Engineers, Business Development Executives, Account Managers and sales operations professionals.


  • Overall 10 years of sales and sales management experience, specifically in technology solutions around software implementation.
  • Minimum 5 years in sales management and directing a team of sales executives.
  • Strong relationships in the media, entertainment, and sports industries. Companies with large amounts of video content are great prospects for Chesapeake.
  • Proven experience developing sales forecasts, overall sales strategy.
  • Knowledge of or prior work experience selling complex technology solutions to the broadcast, media publishing, or digital media space.
  • Familiar with video workflow solutions such as Quantum, Telestream, Squarebox, Primestream, Studio Network Solutions, Veritone, and Archiware.
  • Experience working in tandem with software vendors throughout sales process.
  • Must be familiar with Salesforce or another CRM tool.
  • Must have a bachelor’s degree (BS or BA).

Additional Information

Chesapeake Systems is a leading expert in workflow solutions for the media & entertainment industry built on decades of collaboration with organizations, creatives, and IT teams. As a video systems integrator and consulting firm, we help our clients find the best way to store, access and monetize rich media content. We understand the complex workflows involved with managing media content from creation to distribution and preservation. We are masters at navigating the technology landscape. Our clients include some of the largest studios, broadcasters, sports and digital media publishers in the country. The highly skilled team at Chesapeake designs and implements high-performance, scalable and reliable solutions from storage and asset management to workflow automation, and much more.

Established in 1990, Chesapeake Systems is headquartered in Baltimore, Maryland with satellite locations in New York City and Los Angeles. We are a full-service provider of technology systems and solutions that specializes in optimizing media workflows from creation to distribution and preservation. Chesapeake’s expert architects design pioneering asset management solutions that enable creative teams and drive efficiencies in IT, all backed by steadfast customer support.

At Chesapeake, we believe in fostering a creative mindset to solve technology problems for our clients. This is a very coaching-oriented culture. We look at problems as challenges and want our teams to collaborate to come up with the best solutions for our customers.

Apply Now - Director of Sales

  • Accepted file types: pdf, doc, docx, txt, rtf, pages.
  • Accepted file types: pdf, doc, docx, txt, rtf, pages.
  • This field is for validation purposes and should be left unchanged.