Round Square Worldwide Management Team

The work of the Round Square Community is supported and co-ordinated through the Worldwide Management Team (WMT) which reports to the Board of Trustees through the Chief Executive. Working from Round Square’s registered office in Windsor in the UK, the Team combines specialist support roles with on-the-ground co-ordination in the territories in which Round Square schools are based.

Rachael Westgarth

Rachael Westgarth, Chief Executive

Round Square CEO, Rachael Westgarth leads the Worldwide Management Team, reports to the Board of Trustees and works closely with the RS Membership to shape and implement Round Square’s strategy and direction. Having coordinated development of Round Square’s current strategic plan she has led a range of initiatives in recent years, including a collaborative research programme with leading universities, the inception and launch of the RS Discovery Framework and the creation of Round Square's Heroes of Discovery for Early/ Primary Years. Rachael represents Round Square at international forums, and promotes the Round Square ethos on conference platforms around the world. A graduate of Oxford University, her career spans non-profit and commercial leadership roles in research, marketing, fundraising, program development and curriculum design.

Jane Howison, Company Secretary

Jane has been involved with Round Square for more than 30 years, initially as bursar at a Round Square member school, and subsequently as a member of the Worldwide Management Team. Throughout Jane’s career with Round Square she has held a variety of posts including Business Manager and Head of Membership. In her current role she supports the CEO in all aspects of her work. Jane is also Secretary to the Board of Trustees.

Pete Singleton, Operations Director

Having served 13 years on the Senior Leadership Team at the Duke of Edinburgh's Award. Pete a long-time fan of Kurt Hahn. Prior to DofE Pete's work focused on experiential learning and application of adventurous activities to engage young people from challenging backgrounds. Pete has run in-school skills development programmes, international expeditions providing service projects to local communities, and has led business and product development for curriculum study and activity centres in the UK and France.

Craig Carolan

Craig Carolan, Professional Development Director

Previously Headmaster & CEO at Stanford Lake College, a Round Square School, and most recently our School's Support Director in Africa, Craig leads Round Square's Professional Development for educators across our global community. Craig is also the main point of contact for RS schools and new enquiries within the Africa Region, where he supports on strategic planning, promotes and facilitates collaboration, and mentors integration of Round Square themes and practices within the region's schools.

Ian Crossland, Schools’ Support Director – Americas

We are delighted to announce Ian Crossland as our new Schools’ Support Director for the Americas Region. Most recently, as Head of School at Park City Day School in the USA, and, before that, Colegio Los Nogales in Bogota, Ian brings first-hand experience of introducing Round Square to two school communities, as well as implementing plans and programs to bring RS to life in a school. Over the past two decades, Ian has worked in a wide range of educational settings (U.S. public/private schools, an international school, universities, online) and in a variety of roles (head of school, division director, classroom teacher, district administrator). Prior to that, Ian began his career as a lawyer, after graduating from the University of Washington School of Law. He returned to university to complete his Masters in Education in 2006 at the Harvard Graduate School of Education.

Ben George, Schools’ Support Director – Australasia & East Asia

Ben guides and supports development and collaboration between Round Square schools across Australasia and East Asia. Previously one of the Founding Team and Director of Co-curricular Programmes at UWC Changshu China, and Operations Director for Higher Ground in Australia, his 20 years leading experiential learning includes roles with Outward Bound and at RS school, St Paul’s Co-educational College in Hong Kong. Regionally, Ben has led development and implementation of experiential programmes and frameworks focusing on character development, design-thinking, sustainability, and wellbeing.


Rajbir (Bubbles) Sandhu, Schools’ Support Director - South Asia & the Gulf

Bubbles has been associated with Round Square for almost two decades as the Rep at Vivek High School, India and more recently as RS Mentor and Coordinator for the SAAG Region since 2013. A former Head of school with teaching experience in both the secondary and tertiary sectors, she works closely with our Regional Trustee and Reps’ Representative in South Asia and the Gulf to support collaboration within the network, respond to Membership enquiries and guide development of Round Square in new and existing Candidate and Member schools throughout the South Asia and Gulf Region.

Aimee Theodore

Aimee Theodore, Schools’ Support Director – Europe and the Mediterranean

As Schools’ Support Director – Europe and the Mediterranean, Aimee is the main point of contact for RS schools and enquiries within the Europe and Mediterranean Region. In addition to supporting schools’ strategic planning and integration of Round Square themes and practices within the region, Aimee also provides practical guidance, support and co-ordination for schools across the RS global community that are working to embed Round Square within the curriculum. Previously Head of a UK Middle School, Aimee’s teaching career spans 17 years and includes working on a national curriculum project across multiple states in Australia. Aimee gained her Masters of Education in Australia and moved to the UK in 2009.

Florencia Marante, Student Engagement Manager

Florencia joined Round Square in 2018 in the newly-created role of SSD for Latin America. She works closely with our Regional Trustee and Reps’ Representative in the Americas to support collaboration within the network, respond to Membership enquiries and guide development of Round Square in new and existing Candidate and Member schools throughout Latin America. Florencia is also a member of faculty at Belgrano Day School in Argentina, a Round Square School, and has a background, and holds degrees in both education and Journalism, Marketing and Public Relations.

Rox Khan

Raksana (Rox) Khan, Finance Manager

Rox manages all aspects of Round Square’s financial management, and works closely with the CEO to draft budgets and produce financial reports for the Round Square Board of Trustees. A qualified accountant with over 10 years’ experience gained in both Corporate and SME businesses, Rox is well-versed in all aspects of accounting Auditing, Commercial, Financial and Management.

Lydia Eckstein, Research Manager

As Research Manager, Lydia leads Round Square’s research projects and coordinates relationships with our University partners. Lydia has a long-standing involvement with Round Square over a number of years as RS Coordinator at ICS Zurich in Switzerland and an established track-record in research, most recently focusing on character education. Lydia gained her PGCE at UCL Institute of Education and holds an MA in International Education from the University of Bath. Her career spans roles as Personal Development Coordinator, Service Learning coordinator and teacher in a range of international settings including the UK, Turkey, Thailand and Switzerland

Sarah McGill, Executive Assistant to the Chief Executive

As Assistant to the Chief Executive, Sarah works closely with Rachael on her day to day priorities, including key initiatives, such as the RS Heroes of Discovery, event planning for the RS Heads’ Symposium, and coordination of Round Square's Conference Calendar. Prior to joining Round Square, Sarah had worked as a PA/EA, for Oracle Corporation, Microsoft, and Wolseley Group, and is an accomplished global project and event manager. Early in her career Sarah was based in Bahrain, working for Gulf Air. More recently she ran her own business, and ventured into the non-profit sector as Senior Fundraiser and Marketing Manager for a youth charity.

Stacey Oguna, Digital Assistant

As Digital Assistant, Stacey Oguna supports Round Square’s virtual programmes and online communications activities. Her role includes updating Round Square’s websites and Intranet, managing our google groups, coordinating social media campaigns and supporting Virtual Conferences and other online student events and programmes. A graduate of Cardiff University, Stacey joins us from her previous role as an Administrator at Public Health Wales. Prior to this she worked on Social Media for catering company Let Them See Cake and has an Instagram page where she shares her own recipes.

Jason Harrison-Miles, Marketing Director

In true Round Square spirit, Jason's start in marketing came through learning-by-doing, when he was asked to promote classes whilst teaching English in Japan. Since then, he has acquired more than 20 years of marketing and communications experience in schools and education charities. Most recently he was responsible for admissions and marketing at City of London Freemen’s School. Jason focus is on increasing visibility of the Round Square Network, celebrating the great work being done in Round Square Schools and working out fun ways of engaging students in our communications activities. Jason oversees and coordinates Round Square’s public-facing communications, including via our website, and Social Media channels, and developing support materials to assist schools in making the most of their Round Square Membership in your own Marcoms activities.