Diana le-Cabrera

Diana Le-Cabrera serves as the Head of School at Guidepost Montessori since June 2025, leading a team dedicated to fostering an inclusive Montessori environment for children from toddlers to 6th grade. Previously, Diana held multiple roles at Higher Ground Education, including Regional Operations Lead, where support for school leaders was provided in various operational areas across Florida and Alabama. Diana's extensive experience includes positions in educational consulting, operations management, and teaching, primarily through Kaplan Test Prep, where strategic oversight ensured high-quality test preparation services. With a strong background in music therapy and health sciences, Diana has also contributed to community initiatives and educational programming throughout a career that spans over a decade.