Senior   Leadership Team

HEADMISTRESS

Rachel Bailey was educated at Badminton School for Girls and Haberdashers’ Monmouth School for Girls. She read Economics at York University and completed her teacher training at Warwick University.

Rachel joined Benenden as Headmistress in September 2024 from The Royal Masonic School for Girls where she was Head of Senior School. She is an experienced educational leader with a clear track record of delivering a holistic education centred on strong academics while building the confidence, resilience and self-esteem that are so necessary for life and work in the 21st Century.

She sits on the HMC Education Committee, is a Governor at The Granville Prep School, and serves as Chair of the GSA South East Division.

Rachel is an accomplished musician and music aficionado. She is also passionate about horses and more recently has been developing her creative side learning the intricacies of cake decorating.

FIRST DEPUTY

Steve began his career as a Maths teacher at the Royal Ballet School, which evolved into also teaching Physics and Computing. From there he went on to become Head of Mathematics at Runnymede College in Madrid, an independent co-ed school, where he taught A Level as well as the International Baccalaureate. Moving back to the UK in 2002, Steve joined the Licensed Victuallers’ School in Ascot, where he progressed from Teacher of Maths to Head of Department. Alongside this role he also established and ran a number of successful businesses in the IT and security fields.

He joined Benenden in 2012 as Assistant Director of Studies with a brief that included line management of several subject areas, monitoring and analysis, the use of technology and online safety. He was then made First Deputy in 2017.

GROUP STRATEGY OFFICER

After completing his degree in Civil Engineering, Matt joined the Army and served for 11 years as an officer in the Royal Engineers and Queen’s Gurkha Engineers. He completed a number of overseas postings in Kuwait, Iraq, Kosovo and Germany as well as working as the Project Engineer for the Gurkha Welfare Trust School’s Project in Nepal.

His last appointment in the Army was as a Vice Principal responsible for leadership and personal development at the Defence Sixth Form College Welbeck, which led to a career change to teaching. On leaving the Army he took up a Physics teaching appointment at Cranleigh School before moving to Christ’s Hospital, where he taught GCSE, A Level and IB Physics alongside being a Houseparent for six years.

Matt Joined Benenden in 2015 as Assistant Head (Co-curricular), moving to Deputy Head (Staff and Co-curricular) in April 2017. From September 2018, Matt took on the role of Director of International and Strategic Projects, overseeing all aspects of the School’s international school partnerships as well as working on other School strategic educational projects.

He also works alongside the Director of Partnerships on the strategy for the School’s Partnership Programme. In 2018 Matt completed a Master’s in Education Leadership.

DIRECTOR OF BOARDING

Lucy joined Benenden in 2008 as Head of Lacrosse and PE teacher, after studying Sport and Exercise Science at Loughborough University followed by Exercise Physiology at James Madison University in Virginia, USA.

After joining Benenden Lucy swiftly became involved in the boarding side of the School, initially as a Deputy Housemistress in Founders and then as Housemistress of Echyngham.

Alongside her role in the boarding house Lucy continued to play Lacrosse internationally, becoming England’s most capped player before hanging up her boots in 2019.

DEPUTY HEAD – ACADEMIC

Helen joined Benenden in September 2021.

Helen is an experienced senior leader, having worked as a Deputy Head in a number of independent schools across the UK. Her interests in the academic life of schools spans work in curriculum development, preparing young people for the future world of work and ensuring all enjoy a rigorous lifelong learning culture. Previously she has also worked as a global educational consultant.

Her other passion is inclusion, having set up the Schools’ Inclusion Alliance (SIA) and led training and guidance across the multi-faceted strands of diversity.

DEPUTY HEAD – PASTORAL

Charlotte joined Benenden in 2024.

Born and raised in South Africa, Charlotte studied Mathematical Sciences at Stellenbosch University. She then taught at Groote Schuur High School before relocating to the UK, teaching at Bradfield College. Alongside teaching Maths, she also ran a senior girls’ boarding house at Bradfield for 10 years.

She oversees all aspects of our boarding and pastoral care, which is consistently considered among the finest of any school in the UK.

CHIEF OPERATING OFFICER

Carl’s career has spanned senior leadership roles in government and the private sector. He served as a senior civil servant at HM Treasury and Cabinet Office, where he programme managed the Coalition Government’s extensive operational efficiency reforms to government. Most recently he was Managing Director at Wincanton, the UK’s leading logistics and supply chain business, where Carl led large-scale public, defence, infrastructure and industrial sector operations.

Carl joined Benenden in July 2025. He lives locally and is married with two daughters. For ten years he was a governor and Chair of Governors at a local primary setting. Outside work, he’s an enthusiastic amateur musician, beekeeper and cook.

ASSISTANT HEAD – ACADEMIC

Alastair joined Benenden in 2018 as Head of Politics, having previously held the same role at Repton School in Derbyshire. As well as teaching Politics and History, Alastair runs the Debating Society and has had previous roles as Scholarship Mentor and as acting Hm of Elms.

In 2024 Alastair became Assistant Head – Academic.

ASSISTANT HEAD – HEAD OF SIXTH FORM

Simon joined Benenden in 2015 as Head of History after ten years as a Boarding House Master at Cranbrook School.

He has been Head of Sixth Form since 2019 guiding students through their A Levels and pastorally to help them gain places at top universities and grades they can be proud of.

Simon is also a teacher of History and Politics.

DIRECTOR OF DEVELOPMENT

Prior to joining Benenden in 2017, Kyle was Head of Philanthropy for The Prince’s Trust. There he designed and oversaw The Trust’s successful 40th anniversary philanthropic fundraising campaign, securing funding to modernise and rejuvenate the youth charity’s building infrastructure and run an array of educational programmes.

DIRECTOR OF EXTERNAL RELATIONS

After obtaining a degree in Multi-Media Journalism at Bournemouth University, Ian spent ten years working in journalism, including four years as Editor of the Kent and Sussex Courier, and led his papers to several industry awards during that time. He then moved onto a role as a Communications Adviser at a London council before joining Benenden in 2015. In 2018 he achieved a Diploma in Professional Marketing from the Chartered Institute of Marketing.

As well as overseeing the Marketing, Admissions and Communications functions at Benenden, Ian frequently runs sessions for pupils about journalism, branding and marketing.