Oakland School Appoints Lisa Williams as Executive Director

Veteran executive leadership coach and Oakland parent steps into new role to expand enrollment, programming, and community impact for students with learning differences.

FLUVANNA COUNTY, Va., May 22, 2026 /PRNewswire/ -- Oakland School, an independent school dedicated to children with language-based learning differences, has named Lisa Williams as its new Executive Director. Williams, who most recently served as the school's Business Director, brings a rare combination of professional expertise and personal investment to the role — she is also an Oakland parent of more than two years.

The newly created Executive Director position reflects Oakland School's commitment to strengthening every dimension of the school's mission — from enrollment growth and fundraising to its nationally recognized equine program and ongoing professional development for faculty and staff. Williams will work in close collaboration with the Head of Education to advance a unified, student-centered vision.

Working closely with the current Head of School, Robyn Bolling, and Oakland families, Williams has identified four strategic priorities that will guide her tenure: Inclusive Curriculum, Faculty & Staff Development, Equine Program Expansion & Community building and partnerships.

"I am excited to make an impact on the whole Oakland community — educating our staff, transforming lives for students, and supporting the families who trust us with their children. Oakland is a truly special place where kids can thrive in ways they simply cannot elsewhere. I hope that impact inspires more families to explore both our year-round school and summer programs."— Lisa Williams, Executive Director, Oakland School

Williams is a certified Executive Leadership Coach with extensive experience transforming workplace culture through inclusion and belonging. Her deep knowledge of neurodivergent learning differences positions her to elevate professional practices across Oakland's faculty and staff — and ultimately to enrich the experience of every student and family the school serves.

In addition to her coaching background, Williams plans to modernize Oakland's operations, updating the school's technology infrastructure, digital presence, and administrative processes to better serve prospective and current families. Her goal is to drive consistent enrollment growth year over year.

Families interested in Oakland School's day and boarding programs are encouraged to visit www.oaklandschool.org to learn more.

About Oakland School

Located in Fluvanna County, Virginia, Oakland School is an independent day and summer boarding school serving students with language-based learning differences, including dyslexia and dysgraphia. With small class sizes, individualized instruction, and a nationally recognized equine program, Oakland empowers students to build academic skills, confidence, and independence within a nurturing and supportive community.

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SOURCE Oakland School