om Sheppard is the founder of 20 More Students, an enrollment strategy firm that partners with independent schools to strengthen enrollment through clear strategy, aligned leadership, operational excellence, and mission-driven storytelling. Over a 34-year career in independent schools, Tom served as a Head of School, 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 (MA), 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. In 2010, Tom received the Enrollment Management Association’s Bretnall Award for distinguished service. Tom also found great meaning in his role as a trustee at the Storm King School from 2015-2018.