A career detour put Deena Carey on the road to be KCD’s Head of School

By RUSS BROWN Photos By Matt Johnson 

After earning her college degree in chemistry, Deena Carey didn’t begin her professional life with a desire for a career in education. Far from it, really. 

“While many education origin stories begin with, ‘I always knew I wanted to teach’, mine couldn’t have been more different,” Carey says. 

How different? Well, quite a bit. When she was in high school her mother told her that she would make a great math teacher, a suggestion that was quickly rejected. 

“I vehemently objected,” Carey recalled. “I had no interest in teaching, education or waking up for a 7:30 a.m. start to the day.” 

However, a change of heart put her on a path that would eventually lead to her role as Head of School at Kentucky Country Day. A press release from the school said Carey was selected from a “talented and diverse” pool of more than 30 applicants from throughout the U.S. after serving five years as the Associate Head of School at the Isidore Newman School in New Orleans. 

“During her (first) visit to campus, Carey emerged as an experienced, intelligent, and passionate educational leader,” said Board of Trustees chairman Chris Brice in a letter to the KCD community. “Most importantly, (her) education and expertise are matched by her caring nature, thoughtful listening, and depth of character.” 

So how did Carey wind up such a success in a profession she originally had no interest in joining? After graduating from the University of Cincinnati with a Bachelor of Science in Chemistry, she said she felt little fulfillment in lab work and “stumbled into” an opportunity to substitute teach. That unexpected detour became a transformative one. 

“A chemistry teacher, confident in my ability, gave me the chance to lead a lesson on the Ideal Gas Laws,” Carey said. “In hindsight, it was far from perfect, but in that moment something clicked. I was hooked. I had discovered the joy of connecting with students and making complex concepts come alive. Since then, I’ve never looked back, although I still love stepping into a chemistry classroom, joining a lab group, and engaging directly with students.” 

Initially, she didn’t envision herself as a leader. It was only after a decade in the classroom that her focus began to shift and she earned a Master of Arts in Educational Leadership and Administration from George Washington University. 

Over time she had realized the importance of supporting students beyond the classroom, helping them discover new pathways for personal growth and cultivate curiosity about the world around them. She also started to see how supporting teachers and staff could be another powerful tool for student success. 

“I realized that the work had evolved beyond content delivery into mentorship, coaching, and relationship building,” Carey said. “As I stepped back, I recognized that I could have a broader impact by guiding teaching and learning across the school. At my core, I am a scientist -- drawn to inquiry, problem-solving and systems thinking. School leadership offered a new and compelling challenge, supporting a culture of continuous growth and leading others in shaping meaningful, student-centered learning experiences.” 

The move to KCD was a homecoming of sorts for Carey, even though she grew up in Cincinnati, where her parents and her brother’s family still live, and her oldest daughter, Katie, will begin law school at UC this month. 

“My roots in Kentucky run deep, too,” Carey explained. “My paternal grandmother was born and raised on a dairy farm in Maysville and my father was born in Portsmouth. There is a strong sense of Kentucky pride on that side of the family, and it’s been fun reconnecting with distant cousins who still live in the region.”

Carey was hired by KCD last fall and officially started on July 1, but she returned to campus a number of times during the 2024-25 school year and worked with Interim Head of School Jon Kellam to make the transition seamless and effective. She noted that from her first visit, both Louisville and KCD felt like home. 

“The campus is truly one of the most beautiful I’ve seen, and the community could not have been more welcoming,” she added. “There’s a sense of pride, warmth and purpose that comes through in every corner of the school. As someone returning to a region that experiences four true seasons, I’m excited for snow days, crisp fall mornings, and my very first Derby Week. It’s a joy to be joining a city and a school with such strong traditions and vibrant energy.” 

KCD, which was founded in 1972, has a campus of over 80 acres. With 862 students JK through grade 12 and a faculty of 157, it is similar to the Newman School (1,200 students, roughly 250 faculty), which Carey believes helped prepare her for her new job. 

“Both schools are inclusive, mission-driven communities that deeply value the strong relationships between students, families and faculty. That experience gave me a comprehensive view of school leadership and a deep appreciation for the complex, human-centered work of leading exceptional school communities.” 

Asked about her short-term and long-term goals for KCD, Carey mentioned the themes of curious learning, forward thinking and leading together that will serve as her foundation for shared efforts across the KCD landscape. 

“I come eager to listen, to observe, and to ask thoughtful questions that will help me deepen my understanding of KCD’s many strengths and the opportunities that lie ahead. I hope to model a spirit of curiosity that invites reflection, learning and bold imagination as we consider what is possible for our students and our school. 

“KCD is a vibrant, thriving and inclusive community where excellence is expected, character is cultivated and students are prepared not only for success, but for lives of purpose and impact. Like many schools, we recognize that some of the greatest challenges our students will face lie beyond campus. As the world grows more complex, shaped by rapid advances in technology, shifting global dynamics and the evolving role of artificial intelligence, we are called to guide our students with even greater clarity and care. We will remain focused on living our mission and upholding our motto -- Citizens, Scholar, Steward -- with fidelity.”