About Me

Gabby Miles joins Greenfield as Associate Head of School, Upper School Coordinator, and Success Center Coordinator. Outside of school, Gabby enjoys kayaking, gardening, spending time with her family, and tackling puzzles of just about any kind—whether a jigsaw puzzle or a challenging brain teaser. That love of putting pieces together carries into her work as an educator, where she is passionate about helping young people discover their potential, grow in confidence, and build meaningful relationships. Gabby was drawn to Greenfield’s strong sense of community, commitment to academic excellence, and focus on developing the whole child, and she looks forward to partnering with students, families, and faculty to help every student thrive.