Stephen J. Cloobeck, CEO of Diamond Resorts International, aims to become one of the world’s great hoteliers, saying at a media event in New York City this week that he wants to join the ranks alongside Hilton, Marriott and other hospitality innovators.
He gets a chance to prove his worth this Sunday, or at least expand his audience, when he and his company are featured on the season-three premier of the CBS television show “Undercover Boss.” The reality series previously has featured two other hospitality bosses, from Choice Hotels and Great Wolf Lodge.
Founded in 2006, the Las Vegas-based Diamond Resorts is a growing time-share company, with more than 200 resorts in 28 countries. The management team focuses on taking over struggling vacation-ownership properties, sprucing them up and turning them around. Cloobeck, who also is chairman of Brand USA (formerly the Corporation for Travel Promotion), a public-private partnership that promotes the United States as a destination to international travelers, says Diamond Resorts is unlike most traditional vacation-ownership companies in that it operates like an FIT business, uses a points system, and guests can stay any length of time, from one night to multiple months.
This “Undercover Boss” episode shows Cloobeck as new hire “Jack Fisher,” whose ruse is that he is being filmed for another reality show about hating his job and starting over in a new career. His supposed previous job was as a morgue attendant for 20 years. In a disguise that features an obvious wig and make up that took an hour each day to apply, “Fisher” gets trained at a call center in Miami and works in maintenance and at the front desk at three different U.S. properties, in Sedona and Scottsdale, Arizona, and Williamsburg, Virginia.
In keeping with the formula of the show, the segments address some work issues specific to the company, but understood beyond the business’ industry—in this case, problems with call center workers, maintaining brand consistency among properties and how to handle overbookings. There are a few “tense” moments—including a fire and Cloobeck having to stand next to a poster of his undisguised self, a couple heartbreaking ones, and, at the end, pretty amazing gifts to the participating employees.
One of the complaints about “Undercover Boss” is that it rarely shows realistic work situations (which, frankly, can be said about most workplace-based reality TV programs). Another is that it’s primarily a public relations vehicle for the companies that participate. Indeed, there were no mentions in the episode of some problems Diamond Resorts apparently is having with some properties, as referenced in user comments on the show’s website.
Still, the main purpose behind participating in such a show should be to learn how to improve a company’s operations. So what were the major takeaways from the experience for Cloobeck and his management team?
“The biggest lesson learned was how important training is, especially when you have such a large staff with a broad range of education and experience,” says Cloobeck, adding that since filming ended a few months ago, he created a corporate-wide training program to address those needs.
Management also has addressed staffing schedules, technology upgrades, and equipment and supply needs.
Cloobeck, a former bodybuilder who made his fortune as a shopping mall developer, also learned that in addition to focusing on guest needs, you also need to take care of talented and dedicated employees, especially as they may be experiencing family and financial difficulties in their personal lives.
To honor that lesson, Cloobeck launched a charitable emergency fund about two weeks ago, from which needy employees can apply for assistance. “I give away anywhere from $250,000 to $500,000 each year to charities and organizations around the world and realized that there were people I could help right in front of me, in my company.”
Photo: Diamond Resorts
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7 Responses
I love seeing Stephen Cloobeck in under cover
I think more companys should do that I my self is in the Hospitality Business
I have been for many years I love people
I have to say that I do not believe he would have found anything I was missing if he was the EO of the Hotel I work at.
Linda
May 5, 2012
Stephen Cloobeck is not what he may seem from this show. Just yesterday I stayed at the Kaanapalli Beach Club Diamond Resort in Maui. I was handed Mr. Cloobeck’s business card from the front desk regarding my complaint with the technical assistant staff. I had 5 different technicians come into my room one at a time for 2 days and they could not figure out how to make the internet work. I am a single professional woman staying by myself and had men coming in and out of my room up until midnight which was not comfortable or safe. After 2 days of technicians coming in and out, I relocated rooms. I was on a working vacation and it was of the utmost importance to have access to the internet in my room. I was transfered to another room which was very lovely and given a comp meal. I sent an email to Mr. Cloobeck explaining the situation and my stress level for moving rooms and the men in and out. I appreciated my new room but it did not satisfy my situation of losing 2 days of my stay to changing rooms and work staf in and out. I requested compensation of an addition days stay at a Diamond Resort. I also expressed my concern for the lack of tasteful food in the house resturant. I had asked a friend to join me, and neither of us enjoyed our meal.
When returning to my room the following afternoon in my bathing suit, II was locked out of my room and greated by 2 security guards and 3 policman who told me I had 20 minutes to leave the property and never return. I was also cited with a police report and my license and background information copied by the police officer. When I asked what was going on, they said Mr. Cloobeck said I didn’t like the food and wasn’t happy. I was also told if I set foot again on any Diamond Resort anywhere in the world, I will be arrested.
Is that what you call good customer service and luxury atmosphere Mr. Cloobeck?
I hope to publicize this situation and get some resolver. It was humiliating and embarassing.
I stay at many excellent resorts and have never been treated like this. Most resorts ask for coments about your stay, not arrest you for them.
I was undercover boss my first time and what i saw was a boss who was fair to his employee first he was hard on them but at the end he was kind he open door for those people give hem a chance i cry and cry so hard he touch my soul keep up the good work Mr. cloobeck
Sounds like Alison is on a scam for Diamond Resort free stuff to me. But what do I know, I was not there.
I saw the show here in Australia last night and absolutely loved Stephen Cloobeck and his business ethics. BUT I did dissagree with one part. The young lady at the desk who could not even pronounce places where other resorts were, I felt had apart from no training, had absolutely no common sense at all. I am not being nasty, I just find that this is very common in many businesses today. The young ones don’t seem to use common sense and look after the customer. They are the ones paying their wages. I felt Stephen should have addressed this issue also not just the training. She should have tried a lot harder to keep the customer on the line and offer more incentives etc. I thought that maybe if the staff were on some sort of retainer for the amount of bookings they make would help them to work harder and put in more effort. She seemed to have the attitude – easy come, easy go and she lost you a lot of business Stephen.
Diamond Resorts has a class action lawsuit just from their activities at Point of Poipu in Hawaii. The maintenance fees have tripled, they’ve illegally installed DRI employees on the board and are not trying to push through a “water assessment” that is so expensive it defies logic. They have known about the water damage for years and then give owners ninety days to pay thousands of dollars or threaten them with bad credit and liens.
My timeshare week was cancelled less than two months before we are to leave for vacation, even though we’ve paid our maintenance fees, and now my three children won’t get to have the only vacation they get with their parents together this year.
No wonder this guy can afford everything, including a bodyguard… he monetarily rapes the middle and lower classes!
I just loved the show. I believe he is a straight forward person and he is passionate about what he believes and his product. Allison, with a simple “do not come into the room now” you could have avoid the whole sittuation. I believe these gentlemen were trying as hard as it can be to simply make you happy and help you with your problem for you to go trashing the intentions as a non safe environment for you… I mean… Constructive criticisim is good but the whole thing was wrong? If I was him and could , probably would have done the same thing. I worked for 25 years in hospitality and some times , even when we do try our very best and some people even leave family and lifes behind to pursue this passion, to some people it is just not enough and that arrogance because “you are the customer and you should be right attitude ” it is just insulting to the very core of the people you rely the problem to on the first place.