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The Mayor of Pittsburgh, Bill Peduto, does a stint as a municipal employee in the Steel City. During his shifts, Peduto performs jobs as a refuse worker, a carpenter, a self-sufficiency coordinator and a Public Works employee who cuts down dead trees.

CEO/Founder Doug Guller of Bikinis Sports Bar & Grill, who welcomes controversy and proudly refers to his chain of restaurants as "breastaurants". While undercover, Guller contends with a troublesome employee who not only refuses to don the uniform’s bikini top, but also over-serves an intoxicated person.

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Gina Rivera, Founder and President of Phenix Salons INC., a franchise which offers independent salon and business professionals the opportunity to own and operate their own luxury salon suites, goes undercover to see if it will color her perception of how the company is running,

David Seelinger, Chairman and CEO of EmpireCLS Worldwide Chauffeured Services, a luxury chauffeured transportation leader that provides services in more than 700 cities worldwide, goes undercover to see if his company is running smoothly.

Robert Powells, President and Co-Founder of The Rocket Fizz Soda Pop and Candy Shops, the largest candy and soda shop franchise in America, embarks on an emotional journey to discover what keeps his candy shops sweet.

Rick Forman, Founder and CEO of Forman Mills Inc., one of the fastest-growing discount clothing outlets in the country, discovers some defects in his organization.

Jessica Herrin, CEO and Founder of Stella & Dot, a leading global direct sales company with its own boutique-style jewelry and accessories line, goes on an undercover journey to discover the real gems working within her company.

Armando Montelongo, CEO of Armando Montelongo Companies, a top real estate company that specializes in educational seminars that teach wealth creation and financial independence, goes undercover to see what keeps his real estate investment company on solid ground. For the first time in UNDERCOVER BOSS history, Montelongo hires a body double to help conceal his identity while undercover at one of his seminars.

Gigi Butler, Founder and CEO of Gigi's Cupcakes, America's largest cupcake franchise, hopes to discover that her company has the proper ingredients to keep rising to the top. While undercover, the Cupcake Queen crumbles under the pressure of decorating a cake and spirals out of control when an employee fails to top cupcakes with Gigi's signature swirl.

Todd Pedersen, CEO and Founder of Vivint, Inc., a leading provider of residential security and state-of-the-art smart home technology, goes undercover to see how his company is wired, on the sixth season finale. The boss tries not to lose his grip while battling his fear of heights on a customer's sloping roof during a wireless installation, and he faces even more stress when tasked with taking calls at his company's monitoring center for home and commercial alarms.