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.

Courtland Gray, COO of Peavey Electronics, goes undercover to see what keeps his audio empire rocking.

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.

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.

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.

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.

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.

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.

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.

Jose Costa, the Venezuelan-born President of Maaco, goes under the hood to inspect "America's Bodyshop,".

CEO/Founder Doug Guller of Bikinis Sports Bar & Grill, who welcomes controversy and proudly refers to his chain of restaurants as "breastaurants,".

The Mayor of Pittsburgh, Bill Peduto, does a stint as a municipal employee.

John Hartmann, the President and CEO of True Value, one of the largest hardware cooperatives in the world, reactivates his undercover skills from his time as an FBI agent when he investigates the state of the True Value company and employees.