Back for a third round of bosses going undercover in their own companies to see what is and isn't working, Diamond Resorts International CEO Stephen J. Cloobeck was up first on the season premiere of "Undercover Boss" (Sun., 8 p.m. EST on CBS). He took on four jobs at various properties that the relatively new company owns and learned more than he expected.
The company motto, as Cloobeck was so proud of saying, is simply, "Yes." He doesn't want a client to ever hear the word "no," and so he was at a complete loss when working alongside Sarah at the call center.
Not only was she saying "no," but she didn't fully understand the software package she was using, nor was she adequately prepared to handle certain customer situations.
Cloobeck was so beside himself, he broke character and revealed his true identity to her. Sarah was terrified she was going to lose her job, but Cloobeck tried to assure her he saw it as a training issue and not her fault.
She continued to worry, though, until Cloobeck brought her to his summer resort for the official reveal. There, he set her up with a Hawaiian vacation and paid off her student loans so she could graduate with her business administration degree.
The three other people he met and worked with also reaped the rewards of his generosity. Amanda at the front desk got an offer to work in Ireland, where she wanted to be, as well as cash to help pay her mother's medical expenses. Painter Greg got a new hybrid truck, better equipment at work and a cash bonus.
Finally, Cloobeck connected personally with Randy, who worked as a repairman at one of his resorts. Randy had sold a business and wound up losing big on the deal, so he and his wife were both working two jobs now. Cloobeck paid off their mortgage, allowing them both to quit a job, and gave him a cash bonus, too.
Most importantly, Cloobeck felt that he gained some important knowledge about the little things that he was losing sight of with his focus on building the brand and growing the business. He absolutely felt it was a worthwhile experience.
Season 3 of "Undercover Boss" airs Sundays, 8 p.m. EST on CBS.
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Correction: An earlier version of this post mistakenly noted that Amanda was going to work in Italy, not Ireland. It has since been corrected.
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