Grand Cayman Villas & Condos
September 1, 2023
Richmond, Virginia
Job Type
US$100,000 - $125,000 based on education, achievement, and experience.



Who We Are:

Grand Cayman Villas and Condos (GCVC) is an innovative vacation rental company devoted to offering exceptional guest experiences in Grand Cayman. Established in 2003 in Richmond, Virginia, we have carved out a market-leading position in the Cayman Islands hospitality industry with vertical integration into guest/owner services and a commitment to innovate and protect our brand. Our team of 7 professionals in the USA office caters exclusively to Grand Cayman properties, representing only those we've personally inspected and approved. Exceptionally important in our industry is the relationship we have with our owner-partners; without whose properties, we would not exist.

As a tight-knit team of full-time dedicated professionals, we manage an impressive portfolio of 175 properties and operate 6-10 e-commerce websites while also serving as travel agent for another 100 condos. It is our drive and our clear long-term vision to become the go-to partner for marketing and reservations of private villas and oceanfront condos that has led to our success.

What Makes Us Stand Out:

At GCVC, we believe in providing the highest level of service and premium amenities to our guests and owners. Our suite of services includes several Toyota Vans, over 200 kayaks, paddleboards, and water toys, plus a 32 ft. World Cat luxury snorkel charter boat. Our strategic partnerships also serve to enhance the quality of what we offer to our guests and owners, elevating their experience from the moment they book to the day they check out. Repeat guests are our best guests.

We are also committed to our leadership in offering the best in e-commerce technology, software customization, SEO/PPC, and digital marketing. We have in-house web design.

Why Work With Us:

Working at GCVC means being part of a small, talented team passionate about the hospitality industry, and deeply committed to being the very best. With us, you'll have the opportunity to work with leading technology, engage in strategic partnerships, and directly impact our continuous growth.


We’re currently seeking a visionary leader with excellent operational skills to serve in a pivotal role as General Manager.  In this position, you will not only steer the current operations of our organization but also have input into business strategy, marketing to property owners, expansion of services, and property acquisition.

During the first 6-8 months of your employment, your focus will be on gaining a deep understanding of our tools, our product, and property management software, enabling you to drive tangible outcomes and help us stay on top of our game.

Two key areas of your responsibility will be managing our reservation system and the communications between our USA marketing & reservations team and the guest services staff in Grand Cayman. These critical elements will require you to maintain oversight of our operations, guest experiences, and seamless collaboration across our teams.

You can be assured you’re the ideal candidate for this position if you are a confident and experienced leader with an understanding of e-commerce, a track record in delivering results, and a passion for problem-solving. Experience with a leading property management system (PMS) will be essential.

Apply today and seize the opportunity to shape your future while contributing to the evolution of the vacation rental industry in one of the most beautiful Caribbean destinations.


  • Supervision of Richmond, VA staff for marketing, e-commerce, reservations, accounting, & audit
  • Plan & budget for operating company financial results
  • E-commerce analytics and implementation of strategies with outside vendors
  • Draft & edit guest communication templates
  • Meet quarterly on Grand Cayman with owners and vendors
  • Human resources for marketing, e-commerce, reservations, and accounting functions.


  • 4-year college degree minimum, business/e-commerce/marketing major or minor.
  • General management MBA preferred- marketing, accounting, spreadsheet-QA, business policy, finance, OB, e-commerce familiarity
  • Spreadsheet, Presentation & Word Processing Software ability.
  • GCVC uses Apple Hardware & Software as well as cloud-based software programs.
  • Recent experience in the vacation rental industry and familiarity with e-commerce, Google Analytics, SEO/SEM
  • Exceptional written and oral communication skills
  • Being well-traveled in the Caribbean is a plus
  • Must have a US, UK, or Canadian Passport
  • Able to pass a Cayman police clearance examination with no felony convictions in your home country
  • Vacation Short-Term Rental Experience mandatory


Annual Salary: US$100,000 - $125,000 based on education, achievement, and experience.

Bonus: Bonuses are paid to all full-time (USA) employees on April 15 & December 15 as a function of periodic profitability and results also reward strong individual performance on a subjective basis. (Total, Annualized) Bonuses can range from 20% - 40% of Annual salary, plus another 5-10% of total compensation contribution to GCVC profit-sharing 401(k) plan.


  • Paid time off, such as PTO, sick days, and vacation days
  • Retirement benefits or accounts

Schedule: Available during regular business hours as well as weekends and holidays as needed.