August 1, 2022
Anywhere, United States of America
Job Type
Annual salary $60,000 - $70,000 based on experience with an on-track earning (OTE)  $150,000 with no earning ceiling!


Company Overview:
SkyRun Vacation Rentals is rapidly growing and currently facilitates over 20,000 guest reservations annually and manages over 1000 properties across 29 of the most beautiful destinations in North America.  The technology platform that SkyRun has built to manage these reservations, properties, and locations, has grown to be one of the most advanced in the vacation rental industry. This position is a unique opportunity - a rare combination of “in on the ground floor” exposure with an already established Inc 5000 growth trajectory and in the sizzling hot vacation rental industry.

Testimonial from an employee "Liked the open communication and collaboration. Tons of transparency. People were collaborative, great environment. Will continue to recommend SkyRun."

Position Summary:

SkyRun is seeking a dynamic sales leader who will be responsible for identifying sources of candidates that can qualify to become the owner of a SkyRun Vacation Rentals franchise and provide professional vacation rental property management under the license of the SkyRun brand. The Director of Sales assists prospective destination owners through the decision process of purchasing a location, contract signing, and onboarding. This position reports directly to the CEO.

This is a great opportunity for an ambitious, independent, experienced manager/director-level employee who wants to help drive the evolution of how SkyRun disrupts the vacation rental industry. Success in the role requires sound sales processes and strong influencing skills.


We are looking for someone to:

  • Prospect, generate leads, deliver presentations, host discovery days, and close new destination sales.
  • Develop sources and compile lists of future destination owners in the lead tracking system.
  • Source new sales opportunities through outbound cold calls and emails, portal leads, and working with broker networks, as well as incoming lead follow-up.
  • Identify quality candidates and walk the candidate through our sales process. Assist in financially qualifying prospective destination owners.
  • Conduct or assist in the presentation of the advantages, benefits, and salable features of owning a SkyRun destination.
  • Travel as required to potential SkyRun locations and trade shows to call on and meet with future location owners.
  • Collaborate with the leadership to shape and ultimately lead the execution of SkyRun’s expansion strategy.


  • Proven experience building and scaling successful franchise systems is a plus.
  • Proven experience in high-dollar item/long-sales cycle sales with exceptional results required.
  • Competitively driven, a creative strategist who can develop new ways to drive sales and value to existing and prospective SkyRun locations.
  • Vacation Rental experience is a plus.
  • Flexibility to travel as required to trade shows, to call on and meet with future location owners, and to visit SkyRun headquarters in Boulder (if working remotely).


Annual salary $60,000 - $70,000 based on experience with an on-track earning (OTE)  $150,000 with no earning ceiling!


  • Generous PTO policy
  • Sick time
  • Health insurance, with available healthcare spending accounts  (HSA and FSA)
  • 401(k), including company match
  • Basic life insurance policy
  • Long-term disability insurance
  • Fun and Wellness benefit
  • Paid volunteer days
  • Paid parental leave
  • Employee assistance program
  • Phone and internet allowance
  • Additional employee-paid benefits available through payroll deduction