2026-27 AI Series : a Collab with MSA

AI-Ready ADVIS Schools: RAIL Alumni Lessons Learned

Audience: All (especially HOS + AI/Innovation Leads + Division Heads + Early Adopter Educators)

Join Amber Berry, Vice President of AI and Strategy at Middle States, along with a panel of ADVIS alumni schools from the RAIL: Responsible AI in Learning endorsement series for an honest look at what they tried, what landed, and what they would do differently to become AI-ready. 

Participants will explore how member schools are navigating community-wide conversations about AI and will walk away with the RAIL asset template Mission Statement. 

AI-ready schools are built on clarity about mission, not just access to tools. This session is designed to provide a clear sense of how your school can benefit from a change strategy in AI.

Thursday, October 29, 2026 | 8:00-9:30 AM

What Keeps You Up at Night?

Emerging Risks Boards Should be Watching in

2026-27

Justin Perillo, General Counsel, NAIS

What should independent school boards be paying attention to right now and what risks are emerging just over the horizon?

This session will explore the most pressing and evolving risks facing independent schools in 2026, with a focus on the shifting legal and regulatory landscape. Areas of focus will include developments related to DEI, immigration, school choice, and artificial intelligence, and how these issues are creating new challenges for school leadership and governance.

This session will help board members better understand the risks that may “keep school leaders up at night” and clarify the board’s role in providing informed, strategic oversight. Participants will leave with a clearer sense of where to focus their attention, what questions to ask, and how to engage with leadership on high impact risks setting the stage for deeper exploration of risk management frameworks and tools.

About the Presenter

Justin Perillo has served as General Counsel at the National Association of Independent Schools (NAIS) since February 2025.

Prior to joining NAIS, Justin was Vice President, General Counsel, and Secretary at Marymount University beginning in October 2022. With more than 20 years of experience in education law, he acted as a key advisor on policies and strategies that supported the University’s mission. In this role, Justin provided legal counsel to the President, the Board of Trustees, and the administration, ensuring that Marymount navigated legal challenges with a strategic and collaborative approach.

Before his tenure at Marymount, Justin spent 19 years at American University, serving in various capacities, including Associate General Counsel. His expertise spans a wide range of education law issues, including intellectual property, commercial and transactional law, athletics, information systems, student affairs, and scientific research. He also played a critical role in advancing strategic initiatives, such as transforming Title IX and Freedom of Expression policies and expanding the University’s trademark portfolio.

Justin earned both his J.D. and bachelor’s degrees from American University.

Thursday, November 19, 2026 | 8:00-9:30 AM

The Three Modes of Governance: Fiduciary, 

Strategic and Generative

Robert Clothier, Founder & Principal, Clothier Governance Consulting

This session will explain each mode of governance and how each works, with a focus on the mode that most boards don't understand well and don't use enough -- the generative mode.  It will also explain how Boards need to use all three at different times and the risks of using any one mode too often or at the wrong time.  Lastly, it will give examples of which mode is best for which issues that boards commonly face.

About the Presenter

Founder and Principal of Clothier Governance Consulting, Bob Clothier is an experienced advisor on governance practices for independent schools and nonprofit organizations. His work spans a wide array of topics, including board roles, responsibilities and fiduciary duties; board/head of school dynamics; trustee recruitment, orientation and evaluation; board and board committee goals, meetings, decision making, and self-evaluation; committee structures, responsibilities and operations; board officer selection, responsibilities and evaluation; and leadership evaluation and succession planning. He also advises on strategic planning and enterprise risk management.

Bob designs customized governance assessments and workshops that include review of institutional documents, leadership interviews, and interactive sessions tailored to each client. He also supports the revision of bylaws and governance documents to align with best practices.

His school clients include The Haverford School, The Shipley School, The Agnes Irwin School, Hyde School, Overbrook School for the Blind, and Chester Charter Scholars Academy. He has also worked with nonprofits such as Philabundance, The Rock School for Dance, Merion Cricket Club, and Radnor Hunt Club.

For ten years, Bob was as Vice President and General Counsel at Ursinus College, where he was the College’s first in-house counsel and primary advisor to the Board of Trustees and its key committees. Previously, he was a partner at Saul Ewing LLP, where he represented institutions of higher education. He also served on the Board of Directors for the National Association of College and University Attorneys (NACUA).

Bob brings decades of independent school governance experience, including service on The Haverford School’s Board of Trustees, where he chaired the Trusteeship Committee for 10 years. He is a graduate of The Haverford School, Princeton University, and the University of Chicago Law School.

Thursday, December 10, 2026 | 8:00-9:30 AM

Strengthen Institutional Decision Making Through

Enterprise Risk Management

Sarah Fay, JD, Managing Partner, Schwartz Hannum PC
Phillipa Lilienthal, JD, Partner, Schwartz Hannum PC

Enterprise Risk Management (ERM) is a strategic framework that helps schools proactively manage institutional risks consistent with the school's mission, strategic objectives, risk tolerance, and available resources. Effective ERM requires collaboration among school leadership, administrators, and trustees to address operational, legal, financial, reputational, and student safety risks.

In this interactive webinar, independent school attorneys Sarah Fay and Pippa Lilienthal will discuss how to conduct an ERM audit and how to use the process to strengthen institutional decision making, governance, and risk mitigation efforts. Case studies will be used to generate dialogue and highlight real-world situations and practical solutions.

Topics include identifying key institutional risks; prioritizing risks and allocating resources strategically; evaluating policies, practices, and compliance obligations; and integrating ERM into strategic planning and school operations.

About the Presenters

Phillipa “Pippa” Gage Lilienthal is a Partner at Schwartz Hannum PC . She is a trusted advisor to corporate clients and nonprofit educational and cultural institutions, with deep experience in governance, student and employment matters, and investigations. She counsels clients on best practices in Board governance, risk management, and organizational compliance, including policy, handbook and bylaw review. She leads professional development programming for Boards, leadership and employees, and speaks at many professional association conferences in these ever-evolving areas.

A significant portion of her practice is dedicated to guiding educational clients through complex, sensitive issues involving both students and employees. She regularly conducts and manages internal investigations, advises on allegations of misconduct, and represents institutions in student-related litigation and crisis response.

In addition, Pippa represents corporate and education clients in a wide range of employment matters. Her work spans federal, state, and local labor and employment laws, with extensive experience in litigation involving discrimination, harassment, wrongful termination, wage and hour disputes, whistleblower claims, and regulatory inquiries. She drafts and negotiates employment and severance agreements, and helps clients proactively implement policies that support legally-sound workplace environments.

Prior to joining the Firm, Pippa was Counsel in the Litigation, Securities Enforcement, and White Collar groups of the Boston office of WilmerHale, LLP, where she served for six months as Special Assistant District Attorney in the Somerville division of the Middlesex District Attorney's office. She was also an associate professor of European Union Law and Comparative Law at Burgundy School of Business in Dijon, France and Counsel at a Vermont firm specializing in employment law and litigation.

Thursday, January 21, 2027 | 8:00-9:30 AM

Confronting The Changing Landscape in Which

Schools Operate

Thomas Shepard, Founder & Principal, 20 More Students
Peter Upham, Founder, Peter Upham Consulting

As the market surrounding independent schools is changing faster than the Institutions themselves, the incremental change model is common in many schools may no longer be sufficient to ensure long-term sustainability.

Independent schools today are navigating a reshaped student market driven by demographics, government-funded school choice programs, and increased competition from previously unforeseen educational models, a growing demand from families for schools to demonstrate return on investment, and the financial priorities of millennial families. These forces are not limited to schools working to fill seats. They are redefining the landscape for all schools, including those that appear fully enrolled. But they may be more vulnerable than they seem.

This session invites participants to consider the broader forces transforming the landscape in which independent schools operate. Drawing on emerging trends, data, and participant perspectives, attendees will explore how these shifts may require rethinking long-standing assumptions about administrative structure, program design, pricing and financial aid, enrollment strategy, and the role of the board.

Participants will leave the session with both a clearer understanding of the changing landscape and practical ways to respond. Intended outcomes include:

1. Analyze key external forces—including demographic shifts, affordability pressures, and evolving family expectations—reshaping the independent school landscape.
   
   
2. Evaluate the limitations of traditional school models (governance, enrollment, financial structures) in responding to a rapidly changing and less predictable market.
   
   
3. Identify strategic areas for innovation and adaptation, including program design, pricing and financial aid, enrollment strategy, and leadership structures.
   
   
4. Apply insights to their own school context to assess potential vulnerabilities and opportunities for long-term sustainability.

About the Presenters

Tom Sheppard is the founder of 20 More Students, an enrollment strategy firm that partners with remarkable schools to build best-in-class enrollment solutions as they prepare for a future filled with promise. Over a 34-year career in independent schools, Tom served as a Head of School, a trustee, a senior enrollment leader, and, most meaningfully, a teacher, giving him a rare perspective on how enrollment strategy connects to institutional leadership. In 2025, Tom founded 20 More Students to pursue his passion for private school enrollment full-time.

Tom previously led enrollment at Trinity-Pawling School (NY), Stevenson School (CA), and The Lawrenceville School (NJ), where he built teams, reimagined recruitment strategies, and improved yield, diversity, and revenue outcomes. He later served as Head of School or Interim Head at St. Andrew’s Episcopal School (MS), Chadwick School (CA), and University Liggett School (MI), leading strategic planning, innovation initiatives, and major institutional change.

A longtime contributor to the profession, Tom has been glad to share his passion for enrollment by chairing (2015-2018) and serving on the faculty (2008 - 2018) of the Enrollment Management Association’s Admission Training Institute. From 2001 to 2009 Tom also served on the faculty of the TABS Admission Academy. In 2010, Tom was honored to receive the Enrollment Management Association’s Bretnall Award for distinguished service to the enrollment industry. Tom also found great meaning in his role as a trustee at the Storm King School from 2015 to 2018.

As part of his commitment to the enrollment industry, Tom has presented at numerous conferences and professional gatherings across the country, eager to engage with anyone interested in achieving sustainable enrollments. He is also the author of numerous enrollment articles.

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Peter Upsham - bio coming soon.

Thursday, February 18, 2027| 8:00-9:30 AM

Strategic Enrollment

Christina Dotchin, MPA, Vice President of Member Relations, E3N

Session description coming soon.

About the Presenter

As Vice President of Member Relations, Christina Dotchin oversees the Enrollment Management Association’s (EMA) membership, business development, professional development, marketing and communications teams, providing programs and resources for over 1,200 independent schools and over 20,000 members. This includes EMA’s Annual Conference, Global Recruitment Fairs, Annual Reports and Data Dashboards, The Yield magazine, and related strategic initiatives.

In September 2024, EMA and the Educational Records Bureau (ERB) announced their intent to merge, which recently received regulatory approval. Once the merger is finalized in spring 2026, EMA and ERB will merge to become E3n, a nonprofit organization designed to strengthen independent school communities and deliver innovative solutions for schools, leaders, students, and families (E3n.org).

With over twenty years in the education sector, Christina is passionate about EMA’s transformative work to support enrollment professionals, school leaders, community-based organizations, students, and families. As an industry thought leader, Christina has presented at numerous regional, national, and global conferences and events. She is also the host of EMA’s Enrollment Spectrum Podcast.

Before joining EMA in 2016, Christina served as the Director of Admission and Financial Aid at Proctor Academy in Andover, New Hampshire. During her 11 years at Proctor Academy, she was the head coach of the girls’ varsity ice hockey team, the girls’ varsity lacrosse assistant coach, student advisor, and dorm parent. Christina served as the President of the New England Prep School Girls’ Ice Hockey Association and was the New England Tournament Director. Christina holds a Bachelor of Arts (BA) in English, with a minor in education, from Colby College and a Master of Public Administration (MPA) from the University of New Hampshire.

May 2027 | 8:00-9:30 AM

The Road Traveled and the Road Ahead

Debra Wilson, NAIS President

The 2026-27 school year has been an exciting one. We will use our time together to reflect on the challenges and opportunities we saw, and look to the road ahead. Join the conversation to look at trends, such as AI, enrollment, shifts in the higher ed landscape and more, as well as the important roles that trustees play in partnering with their heads of school.

About the Presenter

Debra P. Wilson is the ninth president of the National Association of Independent Schools (NAIS).

From 2019 until 2023, Wilson served as president of the Southern Association of Independent Schools (SAIS), where she led the organization through a period of growth and supported school leaders in her region through the COVID-19 pandemic. Her SAIS role followed 19 years at NAIS, first as assistant director of regulatory affairs and later as general counsel. In that capacity, she oversaw regulatory and advocacy work for the organization, supported schools in crises, advanced best practices in governance, and created dozens of legal advisories along with other informational resources. Before joining the NAIS staff, Debra was a tax litigator at the Department of Justice. 

In addition to serving on the boards of several schools, Debra’s board service includes The Enrollment Management Association (EMA), Global Education Benchmark Group (GEBG), Mid-South Independent School Business Officers (MISBO), and National Network of Schools in Partnership (NNSP).

Speaking frequently on topics such as leadership and governance, school safety and risk, and community health and well-being, Wilson is also co-author of the NAIS Trustee Handbook (10th and 11th editions). 

Wilson received a B.A. in English from Sewanee: The University of the South and a J.D. from the University of South Carolina at Columbia. She is a graduate of the Williams School, an independent school located on the campus of Connecticut College. She is an avid reader, photographer, and cook who loves to be outdoors.