Meet Jenna Boller, star employee at Gladstone Shoe Store in Chicago. Standing a gawky 5'11'' at 16 years old, Jenna is the kind of girl most likely to stand out in the crowd for all the wrong reasons. But that doesn't stop Madeline Gladstone, the president of Gladstone's Shoes 176 outlets in 37 states, from hiring Jenna to drive her cross country in a last ditch effort to stop Elden Gladstone from taking over his mother's company and turning a quality business into a shop-and-schlock empire. Now Jenna Boller shoe salesperson is about to become a shoe-store spy as she joins her crusty old employer for an eye-opening adventure that will teach them both the rules of the road and the rules of life.