STEPHEN J. CLOOBECK, DIAMOND RESORTS
Why the Boss wants to go undercover, again: During his first experience undercover, Stephen learned that it's really up to him to make sure guests are having the best time possible. Having just bought a bankrupt company, he knows that he needs to personally see what needs to be fixed to bring this company up to the diamond standard.
Jobs he will do undercover:
Undercover Guest – Even going undercover as an employee Stephen knows he's not getting the whole picture and the only way to get the whole picture is to check-in to one of his resorts. After a quick but thorough examination of the room, he's able to talk to an employee from housekeeping who doesn't hold back his own feelings about problems at the resort. How will Stephen react when he finds out the problems at the resort aren't just surface deep?
Activities Coordinator – Stephen knows that the Activities Coordinators play a large role in ensuring the guests have a great and memorable time. When a young employee bluntly points out that the uniforms are tired and that the guests notice things like that though, will he be willing to make the necessary changes?
Maintenance Technician – Maintenance is the glue that holds a resort together and if there are problems with maintenance, the guest's experience will suffer. How will Stephen feel when he sees all the shortcuts and band-aids this newly acquired resort has succumbed to under a lack of management?
Spa Attendant – What makes the resort in Mexico so amazing is the spa. This savvy businessman knows that an attendant who makes spa guests happy will help bring in more guests. But when he learns how much this attendant pushes aside to make guests happy, how far will he go to help her?
Front Desk – The last time Stephen went undercover and worked at the front desk, he was very unhappy at some of his discoveries. Even though it hasn't been officially branded as Diamond Resorts, he just wants to verify that the front desk is operating at the diamond standard. After discovering two very big problems, will this hot-headed boss be able to keep his cool when a guest starts to complain about discrepancies on her bill?
RK, Housekeeping: RK is a young father who does his best to care for his only daughter with his housekeeper's salary. He hates that the Brian Head, Utah resort that employs him shirks responsibility when it comes to proper care of the property.
Monique, Activities Coordinator: Monique is in charge of making sure that all her guests have a great time and helps them create lasting memories while on vacation in Palm Springs. She is no-nonsense when it comes to stating her opinion and doesn't settle for second best when it comes to making the guests happy.
Markus, Maintenance Technician: Markus runs the maintenance department in Palm Springs and is always positive, despite having come from a rough background as a former drug addict.
Veronica, Spa Attendant: Born and raised in Mexico, Veronica is in charge of the spa at the Cabo Azul Resort. She is always smiling and is focused on pampering all of her guests, despite an extreme hardship at home, where her young daughter suffers from a double hernia and is in desperate need of an operation.
Stephanie, Front Desk: Young and beautiful Stephanie is one of the faces of the Cabo Azul Resort and Spa. However, lack of training during the transition to a Diamond property has left her unaware of certain procedures and policies. She means well, but she is a work-in-progress for Stephen J. Cloobeck.