Dear Friends,

You haven’t heard from Whitfield in a while—and that’s something we’re changing.

Over the past three years, I’ve had the honor of serving as Head of School at The Whitfield School. During that time, we’ve undertaken some of the most meaningful work in our school’s recent history: reaffirming our mission, articulating our first-ever shared vision, completing a successful reaccreditation process with ISACS, and—most importantly—developing a bold strategic plan for the five years ahead.

That plan is called Whitfield 2030. Created in partnership with our community, and as part of our ISACS reaccreditation, Whitfield 2030 is a five-year roadmap that sets a clear direction for Whitfield’s future. At the heart of the plan are ambitious new facilities and learning spaces designed to support the evolving needs of our students and faculty. These transformative projects are accompanied by a redesigned daily schedule, new academic and elective offerings, expanded global learning opportunities, and a refreshed brand that reflects both who we are and where we’re going.

We’re proud of what we’ve already accomplished, and the energy and momentum you can feel when you walk the halls—but we know that transformation is more meaningful when it’s shared with the full Whitfield community. That’s why we’re launching this series: a collection of stories and updates that invite you to reconnect with Whitfield—not just as it once was, but as it is today, and the school it is becoming.

If you’re an alum, a former parent, a grandparent, a past trustee, or a longtime friend of the school, you are part of our story. And we’d be honored to have you with us for this next chapter.

Chris Cunningham, Ph.D.
Head of School

MEET CHRIS AND HELENA CUNNINGHAM

Leading—and Living—the Whitfield Experience

Chris Cunningham became Head of School at The Whitfield School in 2022, bringing more than 25 years of experience in independent school education and a deep belief in the power of relationships to shape learning. A former English teacher, coach, and Assistant Head at The Lawrenceville School in New Jersey, Chris

holds degrees from Stanford and Duke and is leading Whitfield through a period of bold renewal—including a successful reaccreditation, a forward-looking rebrand, and the launch of Whitfield 2030, the school’s five-year strategic plan for the future.

But Chris’s leadership isn’t confined to meetings and strategy sessions. He joins cross-country runners at practice, and travels with juniors during their Civil Rights Journey to Memphis. He orienteers with 8th graders at Camp Wyman. He suits up for the annual faculty vs. seniors kickball game during the Day of Play—and dresses up as Dumbledore during Spirit Week. He travels to Columbia to cheer on the wrestling team at the state tournament. Whether in conversation or in community, Chris leads by showing up—with curiosity, humility, and care.

Chris’ wife, Helena, is herself a lifelong educator, a costume designer, and a beloved member of the Whitfield community. During her 34 years at Lawrenceville, Helena taught French, coached everything from track to ice hockey, served as department chair and senior class dean, and built a thriving costume design program. At Whitfield, Helena costumes all theatrical productions and is actively expanding the school’s creative capacity—gathering sewing machines for the theater department and launching a new costume design club for students in fall 2025.

Together, the Cunninghams bring warmth, purpose, and presence to Whitfield—leading by example, living the mission, and helping shape a community where every student is known, challenged, and inspired. When they’re not on campus, Chris and Helena enjoy reading, traveling, outdoor activities, and spending time with their two adult sons.