Cool Jobs: Sandals Resorts Executive Leadership Experience with Hospitality

With more than 25 years experience, Wayne Cummings details global career catering to diverse consumers


As the director of business processes and administration for Sandals Resorts International, Wayne Cummings oversees training and staff of all new employees within the company. And none of this is by chance or coincidence.

Having started in the trainee program over 25 years ago, Cummings knows the ins and outs on how to train the next generation of Sandals leaders. Through a structured and streamlined leadership development plan under the company’s corporate university, top performing team members are placed on special programs and initiatives and groomed on a path for future leadership. The program is in keeping with the organization’s history of investing in the development of young people, many of whom are now trailblazers in the regional and global tourism sector.

Since he joined the company in 1989, Cummings has been on the forefront of the hospitality industry—ranging from experiences in a variety of departments including the rooms division, management and administration. spoke with Cummings about his experiences with Sandals, how he’s developing the next group of leaders, and what’s kept him with the brand for more than 25 years. What led you into the hotel industry?

Wayne Cummings: Accident, and a little bit of my interest peaked after having a friend who worked at Sandals Montego Bay. I applied out of interest from hearing from him. I never saw it as a career, I had always thought it as a gap job for a youngster.

You’ve been with Sandals since 1989. What’s the key to your longevity at the company?

Sandals has found a way to fill my job needs. I’ve had 14 different positions within the 25 years, because I started as a training manager, and was being trained for the future. I specialized in the rooms division and with that I became front office manager, room division manager, assistant manager and then I started to heading into trying run small properties, and ultimately I’m now at the head office. Maybe if I was in a static position, I would have done as typical hoteliers do – spend two years here, two years there and then grow through the world. I grew the world through the journey of Sandals. And they’ve kept me busy (laughs). But I’ve enjoyed it.

What are the biggest challenges you face within your role?

As we expand, our cultures are blending. To be Caribbean, its just geography. Other than that, there are nuances of very special things at each place.

[We have to be] systematically revised to accommodate local cultures and standards. I have found us constantly rewriting and redoing our training. It’s easy to follow laws; Its another thing to make sure that the expectations of the local communities are the essence of the property.

Another thing would have to do with government. I wish we found someway to seamlessly allow businesses to have a level playing field. I don’t care whether you’re a foreign entity or not. If we decide we want that business in that country, than we need to facilitate. I spent a lot of time flying around with ministers of finance, and tax departments and I’m always amazed at how they’ve found new ways to tax businesses.

Does Sandals still have the trainee program you started in?

Yes, they do. In fact, its been refined. As a part of my portfolio, I also oversee HR and training.

When I started it was a pretty unorthodox program. You were throw in headfirst and it was sink or swim, but with some structure. What I’ve done with my team is revamped it under the corporate university and provided a clear pathway for their practical journey.

They have to [work with] a minimum of 4 to 5 hotels across the group. As we’ve grown we’re also in eight countries, so the program has to have a minimum of one training manager from each of those countries. When you leave after the two years, you’ve been across the entire group.

Through your travel to different Sandals within the Caribbean, what’s become your favorite destination to travel to?

I like Grenada. I can’t tell you why yet, because I don’t know. I remember going into to Grenada more than two years ago, and just the approach to the island — small and colorful and very Jamaican-esque. But, it seemed to have all the ingredients of success, and they’re far from it. And when you landed, there’s warmth and welcoming from the people that continues to be different. They haven’t gotten to the stage where they’ve taken anything for granted. They remain humble and they remain patient. When we were opening the hotel, the red carpet was rolled out by the government, by the staff…etc. There’s something about their human nature that is just nice. Here [in Jamaica] we call it, “great country people.”

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