Heads & Trustees Week

Heads & Trustees Week | January 11–15, 2027 | Virtual & Recorded

Strong schools are led by heads and boards who work well together. Tailored specifically for Heads of School and Trustees, VAIS Heads & Trustees Week offers five days of focused virtual sessions on the mindsets and skill sets that make leadership teams stronger collaborators and contributors: governing together, aligning on fundraising, using data well, and building stronger boards.

Join live on Zoom each day, or catch up on the recordings when it works for your schedule.

Register now

Register for Heads & Trustees Week

Heads of School and Trustees are invited to join us online January 11–15.

Member: $350

Registration Closes January 8

Register here

How it works

All sessions take place live on Zoom.

Sessions are recorded and shared with registrants, so your head and trustees can watch on their own time.

Keynote: Stretching at Your Collaborative Edges

Collaboration is one of the most frequently used words in education—and one of the least explicitly taught. Our ability to work well together and engage respectfully with one another directly impacts the health of a school community and the well-being of everyone within it. How do we stretch at our learning edges and model the professional behaviors we hope to see in others? How do we take responsibility for our communication, suspend certainty when needed, and build the resilience required for healthy collaboration? Based on Jennifer Abrams’s book, Stretching Your Learning Edges: Growing (Up) at Work, this session explores five essential mindsets and skill sets that help educators become stronger collaborators, communicators, and contributors to their school communities.

About Jennifer Abrams

Formerly a high school English teacher and a new teacher coach, Jennifer Abrams is currently a communications consultant and author. Her many publications include Having Hard Conversations and Stretching Your Learning Edges: Growing (Up) at Work. Jennifer has been a featured columnist on growth and change for The Learning Professional as well as The International Educator, and she keynotes, facilitates, and coaches at schools worldwide. She was honored to be named one of the “18 Women All K-12 Educators Should Know” by Education Week’s “Finding Common Ground” blog.

Monday, January 11
Keynote: Stretching at Your Collaborative Edges
Jennifer Abrams, Author and Educator
Sponsored by ConnectOne Bank

Tuesday, January 12
Greater Impact Together: Leadership Alignment for Fundraising Success
Chris Dudley, AdvancementEDU

Wednesday, January 13
Clean Data, Clear Vision
Eric Heilman, Center for Institutional Research in Independent Schools (CIRIS)
Sponsored by RCM&D

Thursday, January 14
Building Stronger Boards: Orientation, Onboarding, and Re-Boarding
Tekakwitha M. Pernambuco-Wise, Ed.D., Approach

Friday, January 15
Trustee Types: Understanding Self and Others to Drive Board Impact
Damian Kavanagh, Ed.D., MISBO
Sponsored by MISBO

Schedule

Heads & Trustees Week | January 11–15, 2027 | Virtual & Recorded

  • Greater Impact Together: Leadership Alignment for Fundraising Success

    Chris Dudley, AdvancementEDU
    Tuesday, January 12

    Successful fundraising, especially during campaigns, requires true alignment among the head of school, trustees, and advancement leadership. In this session, participants will gain clarity on how a unified case for support, well-defined priorities, and shared definitions of success drive stronger philanthropic outcomes. Heads and trustees will leave with a clear understanding of their distinct and complementary roles, along with practical ways to strengthen coordination and accountability. Whether preparing for a campaign or seeking to elevate ongoing fundraising results, this session will equip school leaders to work together more effectively and achieve greater impact.

    AdvancementEDU founder Chris Dudley served in leadership positions at High Point University from 1999 to 2023. As Senior Vice President for Development, he led a team that raised $450 million in eight years.

  • Building Stronger Boards: Orientation, Onboarding, and Re-Boarding

    Tekakwitha M. Pernambuco-Wise, Ed.D., Approach
    Thursday, January 14

    How can schools select the trustees who will be best prepared to address the school’s strategic needs for the future? In this webinar, we’ll look at recruitment, thoughtful orientation programs, and continual board education for all trustees.

    Dr. Pernambuco-Wise is an executive consultant and certified executive coach who spent 12 years as a head of school. She has served as Secretary on the Board of the National Association of Independent Schools (NAIS) and is the current Board Secretary of the Pennsylvania Association of Independent Schools.

  • Trustee Types: Understanding Self and Others to Drive Board Impact

    Damian Kavanagh, Ed.D., MISBO
    Friday, January 15

    Perfectly reasonable people sometimes shift into surprising patterns when they join boards. Why? This session introduces five recognizable trustee types (Protector, Architect, Interpreter, Insider, and Credential-Seeker) and explores what motivates their behavior. Through examples and generative questions, heads and trustees will examine how different instincts can strengthen board conversations or send them sideways. The goal isn’t to change the people around the board table. It’s to get better at governing together.

    Dr. Damian Kavanagh has been President and CEO of MISBO since 2017, leading the largest regional association for independent school operations professionals.

Sessions

More session details coming soon. Sessions are subject to change.