Author: Kate Caspar

A graduate of Stanford University, Kate brings nearly three decades of independent school experience to her work with students and families navigating the college admission process.

She began her career at Kent School as an English teacher, coach, dormitory faculty member, and assistant athletic director, developing a deep understanding of students both inside and outside the classroom. After earning her master’s degree from Northwestern University, she joined Westminster School, where she ultimately served as Director of College Counseling, guiding students and families through academic planning and highly selective admissions.

Kate later held senior leadership roles at Pomfret School and for 12 years at The Winsor School, where she oversaw grades 5–12 academics, supervised college counseling, conducted mock interviews, and helped shape institutional strategy.

Having worked as a teacher, advisor, college counselor, academic dean, and associate head of school, Kate understands how admissions decisions are made — and how to position students thoughtfully and authentically. Today, she focuses on what she values most: partnering one-on-one with young people to help them tell their stories with confidence and purpose.