Jonathan Caldera is a mission-driven educational leader committed to transforming schools through equity-centered, values-based leadership. With a proven track record across diverse educational landscapes—including Northern Virginia, Upstate New York, and New York City—Jonathan has served in pivotal roles such as Director of Schools, Principal Supervisor, Principal, Assistant Principal, Dean of Students, Instructional Coach, and Teacher. In each role, he has championed academic excellence, student belonging, and adult development.

He has received advanced leadership training from the Relay Graduate School of Education’s National Principals Academy and DC’s School Leader Lab, both of which have shaped his strategic approach to school improvement, talent development, and systems-level change. Jonathan holds a Bachelor’s degree in Music Education from James Madison University and a Master’s in Education from George Mason University.

Rooted in his core values of Love, Loyalty, and Self-Responsibility, Jonathan leads with empathy, purpose, and a relentless belief in the potential of every student and educator. Outside of his professional life, he finds joy playing ultimate frisbee, biking, hiking, and adventuring through local playgrounds with his wife Eva, their children Harrison and Penelope, and their two spirited dogs, Abigail and Teddy.

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