Season three of "Undercover Boss" returned Jan. 15 on CBS. The premiere episode featured Stephen J. Cloobeck, Chairman and CEO of Diamond Resorts International. He implanted his "yes" philosophy into his company and decided to go undercover to test the idea that you never tell the customer "no."
Cloobeck went undercover on four positions throughout the company - maintenance, booking, front desk and painting. Each position featured an employee that Cloobeck, whose undercover identity was that of an eager man interested in the hospitality business named Jack, shadowed to learn how his employees kept to the company's mission.
Randy, Resort Engineer:
The first employee featured took Jack along to update a newly acquired resort. During one of the jobs on maintenance, Jack learned that Randy made a bad business deal in which he lost almost a quarter of a million dollars. The result was he and his wife working two jobs to make ends meet.
Sarah, Booking Agent:
Jack's stint with booking made him realize that there was a serious lack of training in his call centers, a department that received more than half a million calls per year. Jack became so flustered with Sarah's incompetence he revealed his true self as CEO of Diamond Resorts. Cloobeck then had some words with the call center's supervisor.
Amanda, Front Desk:
Jack worked the front desk with Amanda and realized how antiquated the company's resources were with much of the work load being handled by pen and paper. Jack made several notes aloud to Amanda regarding the lack of the computer system. What really touched him was when he learned about Amanda's mother, who suffered from Multiple Sclerosis.
Cloobeck's last undercover job was with Greg, who worked as one of four painters for 800-plus units. It was very apparent to Jack that Greg was shorthanded and worked with inferior supplies. It was really at this moment that Cloobeck discovered that although he built the company he fell asleep at the wheel in terms of training, equipment and staffing.
The highlight of "Undercover Boss" is the finale and the Season 3 premiere was no different. Cloobeck revealed himself to his employees where he talked about his experiences and lessons that he learned while undercover. More importantly, Cloobeck used his financial independence to assist with the personal lives of his employees, including paying off the mortgage of Randy's house and the student loan debt of Sarah.
At first, Cloobeck appears out of touch with his business and is more interested in his personal assets. Toward the end of the episode, Cloobeck comes across as a sympathetic boss who fell out of touch with what got him there.