Bailey Family of Companies becomes women-owned with new leadership

Courtney Bailey Piccolo is the new president and CEO of The Bailey Family of Companies, and Kristy Fasano is its new vice president and chief operating officer, the Pennsylvania company announced.

Over the past few years, Piccolo and Fasano have been working side by side with previous President John W. Bailey as he mentored them for these positions. 

Bailey Coaches
Kristy Fasano and Courtney Bailey Piccolo, of The Bailey Family of Companies.

“I am delighted to welcome my daughter as our new president and CEO,” Bailey said. “I have great confidence that her exceptional leadership skills, strategic insights, and deep industry knowledge, paired with her lifelong commitment to the family business, will steer the organization towards even greater achievements in the future.” 

Redirected company during Covid

In 2020, when Bailey Coach was faced with a 90% loss in revenue due to the effects of Covid-19 on the travel industry, Piccolo and Fasano led the charge to diversify their business and orchestrated the launch of two new ventures, Bailey Automotive Services and Bailey’s Zero Hazard, in an effort to keep employees who wanted to work on the job throughout the pandemic. 

In January 2022, Piccolo and Fasano began acquiring ownership of the company, and today the Bailey Family of Companies is a majority female-owned organization, with Piccolo and Fasano sharing equal partnership. 

With the experience and knowledge gained from starting these businesses, Piccolo and Fasano, along with Piccolo’s brother Josh Bailey, began developing Bailey’s newest business, Bailey Self Storage, which will consist of 56,000 square feet of self-storage on Route 116 in Spring Grove, Pennsylvania. 

Piccolo joined the third generation of Baileys in the family business in 2012, after a successful career in sales at The Hershey Company,  She started her Bailey career at the family’s 87-year-old travel agency, Bailey Travel and Travel Time, where she was responsible for increasing annual sales by $8.7 million. When Bailey Travel and Travel Time was sold in 2018, she moved to the family’s transportation business, Bailey Coach. 

Piccolo is a graduate of Bloomsburg University. She is a member of the Rotary Club of York, where she holds a position on its board and is the club’s president-elect. 

Moves from president to chairman

As Piccolo moves up, John Bailey, the previous president and CEO, plans to semi-retire after 44 years at the helm. He will function as the company’s chairman and looks forward to spending more time with his wife in Florida, playing pickleball, and enjoying his three grandchildren. 

Fasano brings a decade and a half of operational and human resources experience to her position. A graduate of Mercersburg Academy, Pennsylvania State University and Wilson College, Fasano says she is working to promote positive company culture and strong relationships. 

At Bailey’s, Fasano oversees the company’s community service efforts. The Bailey Family of Companies is a Top 100 Contributor for The United Way of York County’s annual fundraiser and is a voting location for Jackson Township. 


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