Meet Jonathan Drummey, Director of Middle School

For Jonathan Drummey, middle school is more than a transitional stage in a student’s academic journey—it’s a transformative moment filled with growth, discovery, and possibility.

"Middle school is where kids are figuring out who they are," Jonathan says. "It’s a magical time when we, as educators, get to shepherd students through that process with care, kindness, and wisdom."

With extensive experience as both a teacher and a school leader across independent and charter schools, Jonathan is deeply attuned to the energy, complexity, and joy that define the middle school years. He sees this time as a pivotal stage of development—where students begin to blossom, deepen their critical thinking skills, and forge meaningful connections with both peers and trusted adults.  

Wildwood feels like a place that reflects the best of what education can be. There's a real sense of humility and forward-thinking here—a commitment to knowing and caring for each child while continually asking how we can do better. - JONATHAN DRUMMEY

"There’s a playfulness and openness at this age that allows for real exploration," he shares. "Our job is to build on that—to help students uncover their strengths, take healthy risks, and stretch into who they’re becoming."

Jonathan’s own educational journey includes a BA in English Literature from Saint Michael’s College, a master’s in Secondary English Instruction from Boston College, and an Ed.M. in Private School Leadership from the Klingenstein Center at Columbia University. Before joining Wildwood, he taught and led in both independent and charter schools on both coasts, including Saint Matthew’s Parish School in Los Angeles and Excel Academy Charter School in Chelsea, Massachusetts.

Drawn to Wildwood’s mission and progressive pedagogy, Jonathan says he was inspired by the school’s thoughtful integration of innovation, curiosity, and community. "Wildwood feels like a place that reflects the best of what education can be. There’s a real sense of humility and forward-thinking here—a commitment to knowing and caring for each child while continually asking how we can do better."

As a division leader, Jonathan sees his role as both a connector and a supporter. "Middle school students are full of energy and creativity, and our job is to create the conditions where both students and teachers can thrive," he says.

Outside of school, Jonathan is an avid cyclist, an enthusiastic sourdough baker, and a self-described car spotter. Most of his time, though, is happily spent with his family—including his three young children—building Legos, playing board games, and making memories at the beach or local museums.