Tom Sheppard brings over 25 years of enrollment expertise and school leadership to his work with independent schools. Over the course of 19 years as a Director of Admission and Dean of Enrollment Management at Trinity-Pawling School, Stevenson School, and Lawrenceville School, he built high-performing teams, reimagined recruitment strategies, and helped schools grow both enrollment and revenue. His work consistently delivered results: stronger yield, deeper diversity, and healthier full-pay ratios.

Tom later served for seven years as a Head of School/Interim Head of School and led transformative initiatives including strategic planning, financial turnarounds, campus master planning, and institutional rebranding. His experience has given him a unique and broad view of how enrollment thrives when school heads, trustees, and leadership teams are aligned around strategy and mission.

A nationally recognized thought leader in the field, Tom received the Bretnall Award from the Enrollment Management Association for distinguished service. He served for a decade on the faculty of EMA’s Admission Training Institute, and earlier, at TABS’ Admission Academy. His committee service includes EMA’s SAO Advisory Committee and Digital Assessment Working Group.

Tom founded 20 More Students to support school leaders and enrollment teams with strategic, sustainable solutions tailored to each school’s culture and market. His work is grounded in a core belief: schools don’t need magic to grow enrollment—they need clarity, strategy, and the right kind of support.