Undercover Boss: The Most Generous Company Giveaways

Undercover Boss focuses on two main things. First, it allows company CEOs to get an honest look at what life is like for the people who work for them by secretly working alongside them, doing the most entry-level, labor-intensive jobs. Second, it’s about giving life-changing news to hardworking employees who deserve a break from their circumstances. Some fans might say it’s also fun to watch the often ridiculous disguises.

Originally thought to be just a business-focused reality TV show, it turns out that Undercover Boss can tug on heartstrings just as much as some of the more emotional shows. From workers sharing their sad stories that involve everything from homelessness to caring for sick children, to CEOs publicly rewarding employees who otherwise felt invisible, there have been some amazing episodes.

8 City Of Cincinnati – $76,000

The Mayor of Cincinnati was determined to learn more about what needed to be done to make the place better, but felt he would only get honest opinions if employees didn’t know it was him they were talking to. So, he went deep undercover, doing a variety of government jobs to get the inside scoop, including working in sanitation.

At the end of the episode, according to Visual.ly.com, he awarded $10,000 each to two employees, one as a gift for their hard work and one to use towards college; made a donation to park recreation programs; bought a new winch for a truck, GPS, and a trip to NYC for another along with spending money; and provided a wheelchair accessible van to the tune of $40,000.

7 MasTec  – $100,000

Power plant and renewable energy construction company MasTec decided to put its CEO undercover on Undercover Boss, which should be ranked among the best educational reality shows. After meeting with all the people who work for the company and toil day in and day out, he felt compelled to give.

The company paid for one employee to have dental work done, which totalled $30,000, according to the Invisible Disabilities Association. Another employee received $20,000 to pay for their wedding along with $25,000 to provide care for their fiance’s sister. The company also set up a $25,000 scholarship in an employee’s name.

6 ADT – $105,000

When ADT’s Chief Marketing and Customer Officer Tony Wells went undercover at the security company, he met people who changed his life as much as he and the company were able to change theirs.

Along with spending $10,000 for the sales team to have a celebration, the company also provided a child scholarship fund of $25,000 and $35,000 donation to one family, according to Security Systems News. There was also a child scholarship fund, money to help one employee pay bills, and more for another to buy a new car.

5 Great Wolf Resorts – $161,000

Great Wolf Resorts, which runs a series of indoor water park resorts throughout North America, decided to provide various employees with plenty of things to show their appreciation. CEO Kimberly Schaefer, the first female CEO to be featured on the show, promoted an employee and gave them six months of paid leave to spend with their young family.

She also paid for one employee to send their child to college followed by knee surgery for another and flying lessons for one, according to Yahoo! Heartwarming stories like these are what makes Undercover Boss one of the best family friendly reality TV shows.

4 Fast Signs – $180,000

According to TVOverMind.com, Fast Signs CEO Carol Monson doled out close to $180,000 from the company to help the employees featured on the show.

The money went towards helping employees pay for medical bills, college funds, romantic vacations, and a honeymoon. But the most significant amount went to one employee who cried after being told he was being given $50,000 for a new house along with a new car to help him with his 2.5-hour commute to work every day.

3 Forman Mills – $250,000+

Most notable among the many gifts bestowed upon employees at the retail chain and department store by CEO Rick Forman was the offer for $250,000 for an employee to buy a home to prevent ever experiencing homelessness again, according to Yahoo! Money.

He also doubled that same employee’s salary and made him head of a new program. Additionally, other employees received promotions, had their cars and kids’ college paid off, and one even got a trip to Disney World with her kids.

2 Modell’s Sporting Goods – $334,000+

Most notable from the episode of Undercover Boss about Modell’s featuring CEO Mitchell Modell was when he had one employee in complete shock after revealing that he was giving her $250,000, according to New York Daily News. The woman had revealed to Modell, who was unrecognizable undercover, that she was living in a homeless shelter with her two children. He was so moved by her story and her uplifting spirit regardless of her dire circumstances. In addition, he gave her a raise. It’s stories like these that encouraged celebrities to appear on a special spin-off version of Undercover Boss, with people like Jewel being among the many musicians who appeared on reality TV shows.

There were three other employees who sat in the hot seat in that episode. Modell gave a promotion to a truck driver along with a $50,000 check and salary increase, a $20,000 check and trip to another, and a seven-day all expenses paid family trip to another.

1 Diamond Resorts – $2.41 Million

After going undercover in several resorts, Diamond Resorts Chairman and CEO Stephen J. Cloobeck was touched by the stories he heard and people he met. He added a program that would benefit all employees of the company with a $2 million crisis fund, according to Patch.com.

However, what was most shocking was the amount of money he gave out to specific employees. Ranging from $15,000 to pay off student loads to $50,000 for one to help care for her disabled mother, and $150,000 to help one pay off their mortgage, the gifts were beyond generous for the lucky few featured on the show.

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