Principal Announcement

Appleby College Appoints David Cresswell as 8th Principal

On behalf of the Board of Governors and the Principal Search and Advisory Committee, we are excited to announce the unanimous appointment of David Cresswell as the next Principal of Appleby College. David will officially join Appleby in July 2027, as the school’s 8th Principal in its 115-year history.

In determining Appleby’s next Principal, the Board undertook an extensive global search, supported by Heather Ring, who leads Caldwell Partners’ Academic, Not-for-Profit, Social Enterprise, and Culture Practice; Appleby’s Chief People Officer, Majella Hillsdon; and a 12-member Principal Search and Advisory Committee. Our reputation as one of Canada’s leading independent schools attracted interest from an exceptionally talented and diverse group of leaders regionally, nationally, and internationally. 

Our extensive community consultations reinforced the importance of finding a leader who can confidently navigate an increasingly complex and competitive global education sector, where the pace of change is both challenging and accelerating. Equally important was identifying someone with exceptional interpersonal skills and the ability to foster and strengthen the warm, inclusive, and caring culture that defines Appleby’s community of students, employees, families, and alumni. This is indeed David.

David also brings approximately two decades of educational leadership, having served some of the United Kingdom’s leading independent schools. He is currently the 11th Headmaster of Barnard Castle School, a co-educational day and boarding school of 600+ students, located in North East England. Prior to joining Barnard Castle, David served as Senior Deputy Headmaster of Whitgift School in London, and has also held leadership roles at both Cranleigh School and Radley College. He is a graduate in Modern Languages from the University of Oxford and received his postgraduate teaching qualification from the University of Buckingham, graduating with distinction. David began his career teaching Modern Languages and Theatre Studies at his alma mater, Cranleigh School, before moving to Radley College to take up the positions of Head of German and Deputy Housemaster. 

An experienced and highly respected leader, David brings a distinguished record of achievement and a forward-looking approach to educational excellence that is strongly aligned with Appleby’s mission, core values, and the priorities identified through our consultations with employees, students, parents, and alumni. Highlights include:

• Developed educational partnerships across China, Hong Kong, Germany, India, and the Persian Gulf, strengthening recruitment, creating collaborative opportunities, and broadening the international outlook of the schools served.

• Established partnerships with universities and sporting organizations while developing new models of engagement with alumni, philanthropy, and commercial activity.

• Launched the Barney Institute of Learning and Innovation with a focus on professional learning, educational research, and leadership development. 

Beyond his professional accomplishments, David is a great supporter of the performing arts and has both directed and performed in numerous theatrical productions. An accomplished athlete, he has competed at the highest levels of field hockey, having captained the University of Oxford team (awarded four Blues) and played professionally in England and Germany.

In appointing David, we also look forward to welcoming his wife, Dr. Aynsley Cresswell, who is a family physician, and their two young children, Olivia and Alexander. The Cresswell family will reside on campus in McLean House and look forward to making Appleby and Oakville their new home. 

“It is an enormous honour to be appointed the next Principal of Appleby College, and my family and I are tremendously excited about becoming part of this wonderful community. 

I have always believed that the greatest gift a school can give its students is the opportunity to discover who they are and become the very best versions of themselves. That means providing an education rich in opportunity, challenge, and support: one that helps young people discover their passions, develop their character, and find a sense of purpose. Above all, it means ensuring that their time at school is not only preparation for the future, but an extraordinary and fulfilling part of their lives today. 

Appleby’s commitment to developing the whole person resonates deeply with my own educational philosophy. I look forward to working with this remarkable community to build on its many strengths and help generations of Appleby students flourish, both now and long into the future.”
   
-    David Cresswell

David will continue to serve in his current role at Barnard Castle School for the remainder of the 2026–27 school year while working closely with Principal Innes van Nostrand, Head of School & Deputy Principal Fraser Grant ’87, and the leadership of Appleby’s Board of Governors to ensure a smooth and effective transition. In the coming months, David looks forward to visiting campus and connecting with members of the Appleby community.

With this announcement, Innes will continue to lead Appleby as Principal until the end of the 2026-27 school year. We look forward to celebrating Innes’ many contributions to the school over the coming months.

We also extend our thanks and sincere appreciation to all members of the Appleby community whose participation helped guide this search, especially our fellow members of the Principal Search and Advisory Committee: Aubrey Baillie ’63, Burhana Bello-Ayorinde, Jas Brar ’98, Andrew Cockwell ’93, Shen Goh ’91, Steven Latimer, Janice Madon, Tracey Pearce-Dawson, Geoff Spidle ’87, and Christine Vasilaros.

Please join us in welcoming David and family to Appleby College!


Sincerely,
 

Dante Morra ’91
Chair, Principal Search and Advisory Committee

Bill Benson ’79
Chair, Board of Governors

Principal Search Resources