Enterprise Sales Director

Sterling, Virginia, United States | Sales and Customer Success | Full-time | Partially remote


At Sestra Systems we deliver smart dispensing solutions to the hospitality industry and count the Washington Nationals, Marriott Marquis NYC and Kennedy Center among our hundreds of customers.  We just completed an oversubscribed round of fundraising and are looking to build our sales team immediately.  We have big growth plans and are recruiting for several Enterprise Sales Directors who are energized by being creative, building relationships and driving revenue.  We are taking a vertical approach so experience selling to stadiums/arenas, hotels and corporate offices is a huge plus.   While this role is very much a ‘hunter’ role, the ESD should be able to work cross-functionally to partner with other Sestra internal teams to achieve their objectives.


The primary goal for our Director is to drive revenue by building pipeline and bringing in new closed-won accounts.  While this role is very much a ‘hunter’ role, the Sales Director will partner with other internal teams to achieve these objectives.

  • Drive sales by utilizing an Account Based Selling model
  • Build and manage pipeline with hands on efforts and collaboration with marketing
  • Own prospecting by utilizing past relationships, cold-calling, networking and more to drive engagement
  • Present Sestra's unique value proposition to decision-makers and influencers to generate buying interest
  • Proactively contribute to building of sales tool kit 
  • Manage and maintain activity and pipeline data in company CRM to enable Sestra to make fast and impactful business decisions.


  • Minimum 8+ years selling a technology solution into the hospitality industry with focus on stadiums & arenas, hotels and/or cruise lines.
  • Deep relationships and established contacts in select verticals 
  • Proven “A” player with high Sales IQ
  • Enterprise sales/complex sales cycle experience
  • Self-starter who works well in a fast-paced environment
  • Strong verbal, written, and presentation skills
  • Demonstrated past performance against sales quota in similar role
  • Bachelor's degree in Business, entrepreneurship, or other relevant major or equivalent experience
  • Sales experience in IoT also a plus
  • Computer proficiency, experience in Excel, Word and PowerPoint
  • Experience with CRM a plus


  • Comprehensive compensation plan
  • Health Benefits
  • 401K
  • Sestra Equity

Our headquarters is based in Sterling, VA. This role may or may not require relocation. The ability to work remotely will be considered for exceptional candidates in desired territories.  Remote sales team members will have a dual responsibility to provide easy, occasional, on site customer support when needed