2026 Virginia C-Suite Awards: CLIFF FLEET

After six years of significant fundraising success, Fleet retired in April as president and CEO of The Colonial Williamsburg Foundation, which runs the world’s largest living history museum. Taking charge during the pandemic, Fleet oversaw a period of financial recovery — including the restoration of Colonial Williamsburg’s A+ credit rating — while advancing preparations for the nation’s 250th anniversary and the foundation’s centennial, both marked this year.

Under his leadership, the foundation launched a $600 million fundraising campaign to support preservation, education and civic engagement, raising more than $560 million, while expanding its digital educational reach to tens of millions annually. During his tenure, the foundation also hosted major conferences and meetings of the America 250 commission and led restoration of the Bray School.

A graduate of William & Mary, Fleet previously served as president and CEO of Philip Morris USA and led 22nd Century Group. He retired April 27 for personal reasons and was succeeded by former Hewlett-Packard CEO Carly Fiorina, the foundation’s board chair since 2020. Conrad M. Hall succeeded Fiorina as board chair in May.

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