Rick Cheshire

I joined GEMS Winchester School Dubai as Deputy Headteacher of Secondary in August 2026, bringing extensive experience of teaching and senior leadership within British and international education. I graduated from the University of Southampton in 2000 with a Master of Engineering degree in Naval Architecture, before completing my PGCE in Mathematics in 2002 and beginning my career in education. I subsequently spent ten years as a Head of Mathematics and have served in senior leadership roles since 2017. As part of my continued professional development, I completed the National Professional Qualification for Senior Leadership (NPQSL) in 2016 and the National Professional Qualification for Headship (NPQH) in 2025.

My approach to leadership is rooted in a simple principle: decisions in schools should always be centred around what is best for students. I believe passionately in very high standards and expectations, and that our young people deserve more than mediocrity. Equally, I believe strong, positive relationships are fundamental to effective leadership. The best schools combine high expectations with trust, mutual respect and a shared sense of purpose, ensuring students feel known and supported while being challenged to achieve their very best.

At WSD, my leadership focuses particularly on academic standards, curriculum, assessment, teaching and learning, and ensuring that students make strong progress from their individual starting points. These expectations extend beyond academic achievement. WSD’s TRUE values of Tolerance, Respect, Understanding our Responsibility and Endeavour reflect the qualities we want our students to demonstrate both in school and beyond it. Education should develop successful learners, but also responsible, respectful and compassionate young people who understand the contribution they can make to their communities.

At the heart of my educational philosophy is the belief that “Nothing is Impossible.” Young people should never allow their current circumstances, previous performance or perceived limitations to define what they might ultimately achieve. With ambition, hard work, excellent teaching and the right support, they are capable of remarkable things.

My ambition for every student at WSD is therefore straightforward: to aim high, expect more of themselves, embrace challenge and leave us having achieved outcomes of which they, their families and their school can be genuinely proud.