If you’ve ever walked the halls of Trinity Episcopal School and felt the warmth, excitement, and sense of family in the air, there’s a good chance you’ve crossed paths with Kailey Leske, our dedicated Enrollment Director. Kailey has been part of the Trinity family for seven years as a parent and six years as a member of the leadership team. Her background is rich with experience in curriculum development, college instruction, alongside years in management and marketing and she believes these roles have prepared her for the dynamic, multifaceted nature of her current work. “I believe we are our best selves when we continue to pursue education as life-long learners,” Kailey says. “My inspiration to be in the world of education is knowing that we are impacting future generations.”

As Enrollment Director, Kailey thrives on connection and storytelling. “I truly believe I have the best role on campus,” she shares. “I love meeting new families, touring them through classrooms, and highlighting what makes Trinity so special. Spring admissions season is my favorite—it’s full of energy and excitement with events, tours, and opportunities to welcome future Patriots. And there’s nothing better than seeing the joy on a student’s face when I bring a new friend to visit their classroom!”

One of Kailey’s most proud contributions is introducing and championing Organized Mass Chaos (OMC), an end-of-year tradition that has quickly become a schoolwide favorite. “When I first introduced the idea, I could see some hesitation. I mean, the name itself goes against everything structured and orderly,” she laughs. “But it has grown into a celebration of joy and togetherness that sends our students off into summer with laughter and memories. Watching my own children experience OMC has made it even more meaningful.”

Kailey’s impact isn’t limited to new families. She’s quick to point out that enrollment isn’t just about growth—it’s about connection. “Enrollment drives everything, but it’s just as important to make sure our current families feel supported and seen. My goal is to help Trinity remain not only a top educational choice in the crossroads area but also a home where people feel they belong.”

Outside of school, Kailey enjoys reading, spending time at the lake, and traveling with her family. Her love of adventure comes naturally—she grew up as a rodeo kid, traveling the PRCA circuit across the U.S. and western Canada with her family while her dad was a professional calf roper. “It was the most amazing childhood I could have imagined,” she says. “Those experiences gave me a deep appreciation for travel and exploring new places with my own kids.”

When asked what inspires her most about working in this school community, she doesn’t hesitate: “Watching our students grow. Seeing the lightbulb moments, the friendships forming, and the joy of discovery—it’s incredibly fulfilling.” This year, she’s especially excited to watch the school’s MAP Growth data unfold, providing insight into the progress and development of each student.

Kailey describes Trinity in three words: intentional, joyful, and inspiring. Her advice to new families is simple but powerful: “Get involved. Show up to birthday parties, school events, chapel. The more you plug in, the more you’ll discover what makes Trinity so special.”

And if there’s one quote that drives her? It’s this: “Good is the enemy of great.” She explains, “It’s easy to fall into routines or feel comfortable with how things are. But I’m always asking—how can we make this better? How can we improve? Whether it’s a tour, an event, or the way we welcome new families, I want everything to reflect the heart of who we are.”

In her role, Kailey Leske helps build the bridge between Trinity and the families who make our school thrive. Through her passion, creativity, and commitment to excellence, she’s not only helping to grow our enrollment—she’s helps to grow our community, one Patriot at a time!