Heads of School Conference
2027 Theme: Building What Endures
Heads of School Conference | January 24-26, 2027 | Williamsburg Lodge, Williamsburg, VA
Steering an independent school requires strategic foresight, resilience, and a trusted network of peers who truly understand the complexities of the role. Set against the historic and restorative backdrop of the Williamsburg Lodge, the 2027 VAIS Heads of School Conference offers a dedicated space to step away from the immediate demands of campus life and focus on the future. This year’s theme, Building What Endures, centers on the foundations, pathways, and systems that carry a school forward long after any single year or leader.
Over three days structured around connection, leadership, and collaboration, you will experience an immersive keynote, hands-on workshops, a collaborative Heads Panel, and ample time to share insights during session breaks, receptions, and meals. Whether you are navigating shifting educational paradigms, strengthening organizational health, or simply looking to recharge alongside fellow leaders, you will leave equipped and inspired to lead your school community forward.
Building What Endures
Leading Through Foundations, Pathways, and Systems
Foundations: Take an honest look at the institutional health your school stands on: enrollment, finances, culture, and governance.
Pathways: Chart the road ahead for your school and your own leadership, alongside heads who have walked it.
Systems: Build the teams, structures, and practices that let good work outlast any one leader.
The DEFCON Scale for Independent Schools: Strategic Response through Clarity
Independent schools face a wide spectrum of institutional challenges, ranging from enviable waitlists to existential financial threats. In this dynamic keynote session, industry experts Dr. Damian Kavanagh and Ross Peters introduce the Independent School DEFCON Scale—a powerful diagnostic framework designed to evaluate organizational health using critical indicators like enrollment trends, fundraising, debt structure, mission delivery, and faculty retention. Together, they will guide school leaders through auditing their current institutional health and applying targeted leadership responses, from calm optimization to urgent triage. Attendees will leave with practical tools to cut through noise, confront reality, and lead their boards and administrative teams in data-informed conversations about risk, resilience, and strategic clarity.
This session is led by two seasoned veterans of independent school leadership who bring decades of combined insight to the stage. Dr. Damian Kavanagh, Ed.D., CAE, brings comprehensive expertise as the President and CEO of MISBO, the nation’s largest regional association dedicated to independent school business and operations. With a background that includes overseeing accreditation and membership for SAIS and facilitating nearly 1,000 workshops, Damian offers a 360-degree perspective shaped by his deep experience as a former teacher, coach, and administrator.
He is joined by Ross Peters, the founding partner of EXPLO Elevate, who specializes in strategic vision, leadership development, and organizational culture. A veteran educator, Ross has held senior leadership roles across top institutions—including Providence Day School, Asheville School, Hawken School, and The Westminster Schools—and has served on the board for the National Association of Independent Schools (NAIS). Notably, Ross brings strong local roots back to Virginia as a proud alumnus of VAIS member St. Christopher’s School. Together, these two leaders will equip you with the clarity and adaptability needed to ensure your school continues to thrive.
Register for Heads of School Conference
Heads of School, along with their partners, are invited to join us in January at the Williamsburg Lodge.
Heads of School: $895
Spouse/Partner Sunday Dinner Only: $195
Spouse/Partner Full Registration: $395
Registration Closes January 8
Book your room for Heads of School Conference
We have reserved a room block at the Williamsburg Lodge for attendees.
Block Closes January 8.