Matthew Gilliland, 31 / Director of Enrollment Management and Strategic Initiatives, North Cross School
Matthew Gilliland oversees enrollment, communications and financial aid at North Cross, leading a team that manages a $2M+ need-based financial aid program and supports JK–12 admissions. He increased overall enrollment by 8.6% in his first year and achieved record enrollment for four consecutive years, while also serving as a strategic advisor to the Head of School on long-term initiatives.
Previously, Gilliland led international recruitment efforts, growing North Cross’s international student body and expanding representation from three to 17 countries. He also contributes to the broader education community through board service with Stuart Hall School and the Montreat Development Foundation, speaking engagements with local chambers of commerce and volunteer work with organizations supporting adults with intellectual and developmental disabilities.
“The students of today are the driving force behind Roanoke’s tomorrow,” he says. “We are dedicated to the daily work of mentoring these young people, ensuring they graduate as honest, community-minded critical thinkers — ready to lead here in the Valley or wherever their paths may take them.”
- M.B.A., Kenan-Flagler Business School, University of North Carolina–Chapel Hill
- B.A. in Political Science, Davidson College
Community Involvement
- Board of Governors, Stuart Hall School (Staunton, VA)
- Board Member, Montreat Development Foundation (Montreat, NC)
- Eagle Scout, Boy Scouts of America
- Volunteer, Camp Joy Virginia — supports adults with intellectual and developmental disabilities
- Presenter, Salem Rotary Club and Smith Mountain Lake Chamber of Commerce — speaks on education access and strategy
- Advocate for Accessibility in Education — oversees North Cross’s $2M+ financial aid program to expand access for families
What inspires you to build your career in the Roanoke Valley?
“While the mountains that surround us are beautiful, it is the people in Roanoke that inspire me to build my career here in the Valley. Roanoke is full of fantastic individuals who represent a unique blend of industry, from healthcare to technology to the outdoors. We have a thriving economy and a community that is committed to the success and sustainability of Roanoke.
Additionally, I would be remiss if I did not mention the North Cross School community as a major inspiration for my place in the Roanoke Valley. We have fantastic teachers at North Cross and I get to work with all my remarkable colleagues who are passionate about educating, coaching and mentoring the future of Roanoke, the region and the world. I also have the opportunity to interact with, mentor and learn from our students each and every day. They are inquisitive and engaged learners who are growing up in this great place and will always call it home.”
How do you hope your work or leadership will shape Roanoke’s future?
“I believe that having a strong independent school option in Roanoke is great for the whole Valley. We have tremendous teachers and administrators that work tirelessly every day to provide a world-class education right here in the Roanoke Valley. We are graduating young people each year who go on to live out our mission of becoming intellectually curious learners who think critically, act with integrity and lead with courage.
Through our financial aid program at North Cross, we award over $2 million each year in need-based financial assistance to ensure that students from across the region have access to an independent school option. Families in and around Roanoke are able to afford a North Cross education and I take great pride in the work we do to make that a reality. The diversity, socio-economic and otherwise, is part of what makes North Cross a vibrant community.
The students of today are the driving force behind Roanoke’s tomorrow. We are dedicated to the daily work of mentoring these young people, ensuring they graduate as honest, community-minded critical thinkers — ready to lead here in the Valley or wherever their paths may take them. The most powerful way to understand this mission and its impact on the community is to see it firsthand. I personally invite you to reach out and schedule a visit to experience the tremendous energy and commitment of the North Cross community. We look forward to welcoming you to campus!”
From the Nomination: “Matthew has made a profound and quantifiable impact on the Roanoke community, particularly by expanding access to top-tier private education for a diverse range of children and families. His work is not merely about growing a school; it is about enriching our community by providing critical educational opportunities that directly benefit our future generations. As a critical thought partner to the Head of School on long-term strategy, Matthew demonstrates his commitment to the sustained growth and success of a vital Roanoke institution. He leads cross-departmental strategic initiatives that are aligned with the school’s goals, ensuring that North Cross remains a leader in education and a valuable asset to the community. In short, Matthew Gilliland is an exceptional leader whose work directly and positively impacts the Roanoke community by enhancing access to high-quality education. His efforts in growing enrollment and managing a significant financial aid budget have created opportunities for countless children, while his strategic initiatives are building a stronger and more diverse institution for the future.”
