Colonial Williamsburg CEO retires, is replaced by Fiorina

Colonial Williamsburg Foundation President and CEO Cliff Fleet has retired, and former presidential candidate and longtime foundation board chair Carly Fiorina has succeeded him, effective immediately.

Fleet has led the living history museum for the past six years and is departing during a significant time for Colonial Williamsburg as it celebrates its 100th anniversary and the United States’ 250th birthday this year. Before joining the foundation, Fleet was CEO and president of 22nd Century Group and president and CEO of Richmond tobacco manufacturer Philip Morris USA.

Fiorina, a business executive who led Hewlett-Packard from 1999 to 2005, ran for the U.S. Senate in California and as a Republican presidential candidate in 2016. She also was U.S. Sen. Ted Cruz’s running mate later that year during his own unsuccessful bid for the White House. She has served on the Colonial Williamsburg Foundation Board of Trustees since 2017 and has been its chair since 2020. Fiorina also is the national honorary chair of VA250, the state’s organization for the nation’s 250th anniversary commemoration.

“Leading the foundation has been the honor of a lifetime,” Fleet said in a statement Monday. “We have made enormous progress over the past few years thanks to the dedication of an extremely gifted leadership team, talented staff, devoted board of trustees and the heartwarming generosity of donors. I have decided to retire for personal reasons and know the foundation’s positive momentum will continue as it approaches its centennial celebration later this year and into its second century.”

The foundation credits Fleet with several achievements, including restoration of the foundation’s A+ credit rating from S&P Global and raising over $560 million for the foundation’s Power of Place campaign. Leading the foundation during the pandemic, Fleet invested in a digital educational infrastructure that reaches more than 25 million people annually.

“The board is grateful for Cliff’s tireless service to the foundation,” Fiorina said in a statement. “He has made a profound impact on the long-term trajectory of the institution which will benefit future generations. The board and I look forward to continuing the foundation’s important and consequential work, particularly as we prepare for both the July 4 and centennial celebrations.”

In 2024, Fleet was fined $500 for striking and severely injuring a William & Mary student with his car in October 2023. In 2025, the student sued Fleet in Richmond Circuit Court, and a jury trial is scheduled in late July.

He holds four degrees from William & Mary: a law degree, an MBA, a master’s degree in history and a bachelor’s in history and religion. He also earned a master’s in education in 2025 from the University of Virginia.

Colonial Williamsburg will hold several events to celebrate the 250th anniversary of the nation, including live concerts and public readings of the Declaration of Independence on July 4th weekend.