Why I Do This Work

I believe that enrollment is more than filling seats — it’s about helping schools become the very best version of themselves.

After decades in this work, here’s what I know: There is no silver bullet. But there is a path forward — one that’s grounded in clarity, momentum, and deep alignment between mission and market.

I’ve worked alongside heads of school under pressure, enrollment directors doing heroic work with too little support, and boards urgently focused on sustainability. I know what keeps them up at night. I’ve also seen what unlocks meaningful change.

That’s why I started 20 More Students — to help schools build smarter strategies, stronger teams, and more resilient enrollment pipelines. Not through jargon or one-size-fits-all plans. Through partnership. Through practical insight. Through honesty and optimism, even when the road is hard.

I believe in data — but I also believe in judgment. I believe in innovation — but not at the expense of what works. I believe the best enrollment work is deeply human.

And I believe your school can thrive.

About Tom Sheppard

I’ve spent my career helping independent schools grow — not just in numbers, but in clarity, alignment, and purpose.

For 19 years, I led enrollment at Trinity-Pawling School (NY), Stevenson School (CA), and Lawrenceville School (NJ). At each school, I built teams, reimagined recruitment, and delivered real results: stronger yield, deeper diversity, and healthier full-pay ratios. I didn’t just drive numbers — I helped shape narratives and strategies that aligned with each school’s mission and market.

Later, as Head of School at St. Andrew’s Episcopal School (MS), Chadwick School (CA), and University Liggett (MI), I stepped into even broader leadership. I led strategic planning, visioning processes, and campus master plans — all while navigating enrollment from the Head’s chair. That was an invaluable experience. It taught me how enrollment success isn’t just about the admission office. It’s about culture, communication, and having the right people aligned around a shared strategy.

I’ve always believed in giving back to the field. I served for a decade on the faculty of EMA’s Admission Training Institute and TABS’ Admission Academy, and I’ve worked on key initiatives like EMA’s SAO Advisory Committee and Digital Assessment Working Group. I was honored to receive the Bretnall Award from the Enrollment Management Association for distinguished service.

I founded 20 More Students because I know what this work demands — and how powerful it can be when it’s done right. I don’t believe schools need magic. They need clarity, tactics, context, strategy, and support from someone who’s been there.

That’s the kind of partnership I offer. Let’s get to work.