iTrip Vacations
September 24, 2022
Charleston, South Carolina
Job Type
Annual Salary: $80,000 - $125,000



iTrip Vacations is located in beautiful and historic Charleston, South Carolina. We offer vacation homeowners the opportunity to worry less about managing their property while earning more revenue through increased bookings.

We’ve accomplished this by integrating with over 180 listing sites, running an industry-leading marketing program, and delivering fantastic guest experiences that have earned us two significant awards: HIGHEST AVERAGE REVIEW SCORE and MOST REVIEWS PER LISTING!

Our work environment is flexible, constantly evolving, and provides growth opportunities, recognition, and rewards for achieving business results. 

If you’re excited to use your skill and drive to help lead our winning team, we’d love for you to continue reading and see if this position is the next best step for your career.


As our Vice President of Operations, you will report directly to our company's President. You will be tasked with developing and maintaining all our operations team's day-to-day schedules, duties, and responsibilities. This position will require you to be a natural leader who works well with people and can motivate and delegate effectively.

Under your management, your team will be responsible for ensuring each of our vacation homes is sparkling clean, well maintained, and in tip-top shape for every guest and homeowner arrival. We aim for a 5-star review from each and every guest who stays in our vacation homes and will depend on you to see that goal through. 

Accepting this posting will mean that your workday will be very hands-on and require great attention to detail. You’ll need the ability to creatively problem solve as issues arise and have the foresight to integrate ideas and systems that will streamline our operations and improve efficiencies. 


  • Coordinate and manage a team of operations managers across all of our Charleston-area markets.
  • Hire, oversee, train, coordinate and manage external cleaning companies.
  • Inspect and train cleaning companies to ensure all our homes meet a very high-quality standard.
  • Coordinate and manage maintenance issues and repairs through third-party contractors.
  • Liaise with guest services to ensure smooth check-in of guests.
  • Manage distribution of guest supplies to all our vacation rental homes.
  • Resolve (or assist in resolution) operational issues that arise each day.
  • Perform on-call duties for guests or home-related emergencies.
  • Ensure that company policy, protocols, and standards are followed.
  • Analyze company data and look for ways to improve efficiencies.


  • Proven experience as a General Manager, Director of Operations, Vice President, or a similarly relevant role.
  • Previous experience in vacation rentals or the hospitality industry is strongly desired.
  • Experience building and leading high-performing teams, including the ability to recognize and cultivate rising talent required.
  • Computer literate and able to use web-based apps.
  • Ability to work with an extremely fast pace growing company with aggressive growth goals year over year.
  • Understanding of and ability to create healthy organizational culture is required.
  • Bachelor’s degree is strongly preferred.
  • Advanced degree, MBA or similar, preferred


Annual Salary: $80,000 - $125,000


  • Relocation Assistance to Charleston, SC.
  • Paid time off such as PTO, sick days, and vacation days
  • Health insurance
  • Life insurance
  • Dental insurance
  • Vision insurance
  • Retirement benefits or accounts
  • Healthcare spending or reimbursement accounts, such as HSAs, FSAs, and HRAs
  • Long-term disability insurance
  • Short-term disability insurance
  • Employee recognition programs