Stephen Cloobeck of Diamond Resorts International returns to Undercover Boss

Last week Diamond Resorts International appointed David Palmer to president and CEO of the company. Palmer was previously the company’s president and CFO. Additionally, Al Bently, previously EVP – Europe, was appointed EVP and CFO.

Former chairman and CEO Stephen J. Cloobeck is staying on as the company’s chairman. In early 2012, Cloobeck appeared on CBS’s program Undercover Boss in an episode that garnered 16.5-million views – the highest for the show – and was invited back for another episode in November 2012. Cloobeck is the only guest so far in the show’s history to return for a second episode, and he spoke with Hotel Management about the experience.

“They came to me about going back to the show after [Diamond Resorts] acquired four or five new companies,” Cloobeck told Hotel Management. “It was an unbelievably great journey for me as a CEO, and a very successful episode for them.”

The show takes company executives from their desks, disguises them and places them in the midst of their employees to perform regular jobs, often beyond the participant’s skil set, while learning what is going on at the lower levels of their company. “It taught me what was important to running [the] business, which in the end is human capital and paying attention to guests,” Cloobeck said.

The program helped give Cloobeck insight and perspective into areas of hotel operations that are often missed out on by executives. “What I really found out was that our training needed to be better and we needed to help people rise to management positions,” Cloobeck said. “In the past I’ve helped fix broken assets to create a brand, and for us we need to deliver on my philosophy on the meaning of ‘yes,’ and to deliver it 24/7 no matter what.”

Cloobeck was afforded the opportunity to once again join in with Undercover Boss and solve issues in his newly acquired companies from the ground up. “My second episode showed me that I’m the throwback hotelier that ones to block and tackle every problem,” Cloobeck said. 

In his newest episode, Cloobeck entered one of his properties as an undercover guest, worked as an activities coordinator, maintenance technician, spa attendant and manned the front desk. “These companies that we’ve acquired have been working on shoestring budgets and making ineffective decisions, and they have to understand the way we do things,” he said.

Cloobeck has kept in close contact with the employees he worked with in his earlier episode of the CBS program, tracking their progress throughout the company and beyond. “I’d recommend participating in this program to any CEO,” Cloobeck said. “If you want to be the CEO of a company you have to walk the walk and take care of your employees.”