Stephen J. Cloobeck
Chairman and CEO of Diamond Resorts International
Education: Cloobeck has 25 years of hands on experience in development, construction, management, operations, marketing and sales of properties.
Why the boss wants to go undercover: Stephen J. Cloobeck is an incredibly intense CEO with one goal in mind: being the best hotelier in the business. He wants Diamond Resorts International to achieve perfection. Going undercover will allow him to see what changes need to be made on the frontline to achieve this ambitious goal.
Jobs That He Will Do While Undercover:
Resort Engineer: The boss gets his hands dirty when he is put to work climbing ladders and doing resort maintenance. A fire erupts while doing a repair… how will this clean-cut CEO react?
Booking Agent: Good customer service is paramount to this CEO. When he discovers the call center fails to meet his high standards, this boss is forced to take action.
Front Desk: The front desk is the first and last impression you have of your hotel experience. Will Stephen’s reservations skills be up to par when checking guests in and out of his own resort?
Painter: Cloobeck works hands on to help repair one of Diamond Resorts oldest and largest properties. He realizes lack of staff and equipment may be inhibiting his dream of being the best.
Randy, Resort Engineer
Sarah, Booking Agent
Amanda, Front Desk