Tom Sheppard

Tom Sheppard is the founder of 20 More Students, an enrollment strategy firm that partners with remarkable schools to build best-in-class enrollment solutions as they prepare for a future filled with promise. Over a 34-year career in independent schools, Tom served as a Head of School, a trustee, a senior enrollment leader, and, most meaningfully, a teacher, giving him a rare perspective on how enrollment strategy connects to institutional leadership. In 2025, Tom founded 20 More Students to pursue his passion for private school enrollment full-time.

Tom previously led enrollment at Trinity-Pawling School (NY), Stevenson School (CA), and The Lawrenceville School (NJ), where he built teams, reimagined recruitment strategies, and improved yield, diversity, and revenue outcomes. He later served as Head of School or Interim Head at St. Andrew’s Episcopal School (MS), Chadwick School (CA), and University Liggett School (MI), leading strategic planning, innovation initiatives, and major institutional change.

A longtime contributor to the profession, Tom has been glad to share his passion for enrollment by chairing (2015-2018) and serving on the faculty (2008 - 2018) of the Enrollment Management Association’s Admission Training Institute. From 2001 to 2009 Tom also served on the faculty of the TABS Admission Academy. In 2010, Tom was honored to receive the Enrollment Management Association’s Bretnall Award for distinguished service to the enrollment industry. Tom also found great meaning in his role as a trustee at the Storm King School from 2015 to 2018.

As part of his commitment to the enrollment industry, Tom has presented at numerous conferences and professional gatherings across the country, eager to engage with anyone interested in achieving sustainable enrollments. He is also the author of numerous enrollment articles.