With placing Stephen J. Cloobeck, CEO of Diamond Resorts on Undercover Boss, CBS expects to attract viewers who are interested in watching how a big boss is going undercover as a worker in his own company that is involved in hospitality business. Cloobeck rebranded a company that was making loses into a new one, called Diamond Resorts, but is afraid that new affiliated resorts he recently purchased are not adopting his corporate virtues and goals as expected.
Cloobeck is undercover as Jack Fisher, a man seeking a job as a hospitality worker in Diamond Resorts on Undercover Boss. First, he visited a resort in Sedona, Arizona, where he recently purchased a business. During this brief visit he is appointed to help in roof-top air conditioning unit repair works where he meets Ed, a former owner of a local RV repair business.
Later, Cloobeck visits Miami, Florida to uncover that Sarah, to whom he is known as Jack Fisher, not Stephen Cloobeck from Diamond Resorts on Undercover Boss, is not prepared to perform her tasks properly. Actually, he rebranded Diamond Resorts in an “yes” company, which means that all and every requirement of a client has to be met. He reveals his true identity in frustration, telling Sarah’s supervisor that she has to undergo re-training to perform her day-to-day duties properly.
Cloobeck is set to hear some unpleasant comments on the company that he acquired for $5 million five years ago. While visiting Willamsburg, Virginia he is told that many workers are leaving the company because of the frozen wages, and is surprised to see that Amanda, working in a Scottsdale, Arizona-based resort is not using the computer system to do her work.
Then, Jack Fisher is gone and Stephen Cloobeck, the CEO of Diamond Resorts on Undercover Boss, reveals his identity to all his employees, giving away more than $100,000 in bonuses, debt relief financing and other gestures of good will.