Stephen Cloobeck gave up the corporate executive suite at Las Vegas-based Diamond Resorts for two weeks to fix and paint drywall, handle small maintenance projects, and check in guests at a few of his company's timeshare developments.
He came away from the experience with the realization that many of the company's 6,000 workers, despite their jobs, have found hardships during the recession and might need financial assistance.
Rather than give money to outside charities, Cloobeck decided to keep the dollars in house. He created an emergency fund for Diamond Resorts' employees and is starting the 501(c)3 nonprofit with a pledge of $1 million.
"That's probably the most cathartic thing to come out of this experience," Cloobeck said Friday.
Cloobeck's time at five Diamond Resorts locations was filmed for CBS's Emmy-nominated reality series "Undercover Boss," where chief executives in disguise interact with their employees.
The episode featuring Cloobeck is the season premiere. It airs Sunday at 8 p.m. on KLAS-TV Channel 8 in Las Vegas.
According to CBS, Cloobeck's time undercover wasn't without a hitch. While working as an engineer and performing a dangerous task the project burst into flames.
Cloobeck is the second Las Vegas CEO to take part in the series. Last season, MGM Grand President Scott Sibella worked various jobs in the Strip resort.
Initially, Cloobeck turned down the opportunity to be on the program. One of his top executives convinced him the idea could give him some insight into the company.
But there was a challenge.
Cloobeck's photo is at every one of Diamond Resorts' 200 properties in 28 countries. He often visits the locations unannounced. Also, Cloobeck's voice is recorded on hold messages for the corporation.
As such, he spent nearly an hour each day in makeup, putting on a wig, a fake beard and camouflaging his white teeth. Cloobeck went to lengths to disguise his voice. While working the front desk at one property, his corporate photo was actually in the background.
The employees knew Cloobeck as "Jack Fisher," a former mortuary worker.
"It allowed me to have this almost out-of-body experience with our team members to see if they understood our philosophies what we hope to get across to our guests," Cloobeck said. "The young lady at the front desk started talking about the company chairman. I couldn't smile or show any emotion."
While he saw small things that needed "fixing" in the company, Cloobeck said the interaction with employees helped him understand what workers go through.
At the end of each "Undercover Boss" episode, the CEO is revealed to employees and a gift of some sort is bestowed. Cloobeck said the gifts he presented "were the largest ever awarded" on the series.
"The philanthropy I showed was unscripted, impromptu and came from my heart," Cloobeck said. "I did it on the fly. This is my own company, so I had tremendous latitude."
During the filming Cloobeck had to balance three jobs; what he was assigned as the "Undercover Boss," his CEO duties and his role in international tourism as chairman of Brand USA, a public-private company that markets the United States abroad.
"It was the first time I was out of control, without my phone or BlackBerry," he said.
Since promotion for the series began in December, the only negative has been criticism of Diamond Resorts on social media networks by some unhappy timeshare owners. Cloobeck said the comments "are coming from less than 10 people out more than 650,000 members. I would be happy to given them back their money."
Still, Cloobeck would encourage any CEO to participate in the series.
"It's important to get into the trenches and see if systems are working properly," he said.
Contact reporter Howard Stutz at email@example.com or 702-477-3871. Follow @howardstutz on Twitter.