Colonial Williamsburg Leadership Transition: Cliff Fleet Retires, Carly Fiorina Steps In as CEO

Apr 29 '26

If you’ve spent any time in Williamsburg—whether as a resident, visitor, or someone considering a move here—you already know that Colonial Williamsburg Foundation is more than just a historic attraction. It’s the heartbeat of our community, a major economic driver, and one of the most recognized living-history institutions in the world.

This week brought a significant leadership change that will shape its next chapter.

A Leadership Transition at a Pivotal Moment

The Foundation announced that Cliff Fleet is retiring as President and CEO after serving in the role since 2020. Stepping in immediately is Carly Fiorina, who had been serving as Chair of the Board of Trustees.

The timing is notable. Colonial Williamsburg is on the doorstep of its Centennial celebration, alongside major national milestones like the 250th anniversary of American independence—events that will bring increased attention, tourism, and investment to the region.

Fleet described his tenure as “the honor of a lifetime,” citing the organization’s momentum and strong leadership team as key reasons he feels confident stepping aside now.

What Was Accomplished Under Cliff Fleet

Fleet’s time leading Colonial Williamsburg wasn’t just about maintaining tradition—it was about modernizing and strengthening the institution for the long term.

Some highlights from his tenure include:

Achieving national recognition for education, preservation, and civic engagement
Restoring financial strength, including an A+ credit rating from S&P Global
Raising over $560 million for the Power of Place Centennial Campaign
Expanding digital education efforts, now reaching 25+ million people annually

That last point is especially important. Colonial Williamsburg isn’t just a place you visit anymore—it’s a platform reaching classrooms, researchers, and curious minds across the globe.

Carly Fiorina Steps Into the Role

Now leading the Foundation is Carly Fiorina, a name many will recognize from both the business and public sectors. She previously served as CEO of Hewlett-Packard and has been on the Colonial Williamsburg Board since 2017, serving as Chair since 2020.

She’s also deeply tied to Virginia and currently serves as National Honorary Chair of VA250, making her appointment particularly aligned with the moment we’re in.

Her early message signals continuity—building on the progress already made while preparing for the Foundation’s next century.

Why This Matters Locally

From a real estate and lifestyle perspective, this kind of leadership transition is more than just news—it’s impactful to the entire Williamsburg area.

Colonial Williamsburg influences:

Tourism and local business activity
Property values and desirability, especially in nearby neighborhoods
Cultural and educational opportunities
Regional identity and long-term investment

When the Foundation is strong, Williamsburg is strong. And heading into a period that will likely bring increased national attention, having experienced leadership in place matters.

Looking Ahead

Between the Centennial celebration and the 250th anniversary of the United States, the next 12–24 months could be some of the most exciting Williamsburg has seen in decades.

More visitors. More events. More energy.

And for those of us who live here—or are thinking about making the move—it’s one more reminder that this isn’t just a historic town. It’s a place that continues to evolve, invest, and tell its story in new ways.

About Me (And Why I Write These Articles)

If we haven’t met yet, I’m John Womeldorf—also known as Mr. Williamsburg.

I’ve been helping people buy and sell homes across Williamsburg, Richmond, and Hampton Roads for over 20 years, but what I’ve really become known for is something a little different: being a local ambassador first, and a Realtor second.

I write articles like this because when people consider moving to Williamsburg, they’re not just asking about square footage or price per foot—they’re asking:

What’s happening in the community?
Is this a place that’s growing and evolving?
What kind of lifestyle can I expect here?

That’s where I come in.

In addition to real estate, I’ve renovated homes, invested in property, hosted guests in my short-term rentals, and spent years deeply involved in the community. I also regularly help clients with everything from lot selection and builder strategy to navigating neighborhoods, memberships, and lifestyle fit.

If you’re thinking about buying, selling, building, or just exploring your options, I’m always happy to have a conversation.

📞 Call or text: 757-254-8136
📧 Email: John@MrWilliamsburg.com
🌐 Website: mrwilliamsburg.com

And if you’re curious how I tell the story of a home, take a look at my “Every Home Has a Story” series:
👉 https://mrwilliamsburg.com/mr-williamsburg-home-stories/