Steve (Adam Ray) is a charismatic bell captain who leads a tryout on the roof of an upscale resort to determine who will be the next B.I.T. - bellman in training. Once Josh (Josh Zuckerman) wins that honor, he is relentlessly hazed as he learns the ropes. Steve has a crush on the chef concierge Kelly (Kelen Coleman), and tries winning her back by lying about a promotion, but gets caught up in a string of misadventures like when a self-help guru named Gunther (Thomas Lennon) scams guests and the other bellmen, all while keeping up the charade of his promotion for Alan (Willie Garson), the irritable Rooms Division Manager whose hot on his tail.