November 18, 2021
Anywhere, Colorado
Job Type
$120,000 - $150,000 On target earnings 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.

Position Summary:

This is a great opportunity for an ambitious, independent, experienced manager/director-level employee with franchise sales experience 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.

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 destination location 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:

  • Collaborate with the leadership to shape and ultimately lead the execution of SkyRun’s expansion strategy.
  • 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 lead sources and manage the marketing budget for new destination marketing working with SkyRun marketing to implement programs that generate leads.
  • Focus on high-potential unclaimed territories to find the best operator in those areas.
  • Prospect, generate leads, deliver presentations, host discovery days, and close new destination sales.
  • 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.
  • Assist with the initial phases of the onboarding cycle for new SkyRun locations.
  • Travel as required to potential SkyRun locations and trade shows to call on and meet with future location owners.


  • 2+ years experience building and scaling successful franchise systems for leading franchise brands desired
  • 5+ years experience in high-dollar item/long-sales cycle sales with exceptional results required
  • Knowledge of the principles and strategies for building successful franchise systems desired
  • Certified Franchise Executive (CFE) designation desired
  • Outstanding organizational skills and ability to manage all documentation and legal agreements relating to the sale of a license
  • Business case business plan building, budgeting, forecasting, and analytical skills
  • Experience working in a fast-paced, entrepreneurial environment
  • Creative strategist. Developing new ways to drive sales and value to existing and prospective SkyRun locations
  • Good phone skills
  • Vacation Rental experience is a plus
  • Bachelor's degree highly preferred
  • Extroverted personality and the ability to work in a sales environment
  • Personality and behavioral characteristics that provide for an even-handed approach to problem resolution. Ability to handle rejection.
  • 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)


  • $60,000 - $70,000 annual salary based on experience and qualifications with generous commission bonus plan with an on-track earning (OTE) $120,000 - $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
  • Employee assistance program
  • Phone and internet allowance
  • Additional employee-paid benefits available through payroll deduction