Headington School Oxford Headmistress Caroline Jordan has been nominated for the Lifetime Achievement Award in the prestigious 2026 Tatler Schools Awards.
Caroline, who will retire as Headington School Oxford Headmistress at the end of the academic year, joined the School from St George’s Ascot in September 2011 and, by the time she leaves, she will have spent over a third of her life in Headship. During her time at the School, Caroline led the School throughout a global pandemic, providing clear, strategic direction and ensuring every child continued to receive an excellent education and oversaw the successful merger with Rye St Antony in 2024, one of the most significant changes in the School’s over 100-year history.
Caroline has supported significant developments to the School’s curriculum and extra-curricular activities, overseeing exceptional outcomes for pupils and introduced a middle school curriculum which puts choice right at the heart of pupils’ experiences, enabling them to thrive and flourish. This was acknowledged by the ISI in their highly complementary recent inspection report where Headington received ‘a significant strength’ for the ‘high quality, broad and flexible co-curricular programme’ she has nurtured.
Under her leadership there have also been major developments to the site including a new Dance and Fitness Centre, Library, revamped Sixth Form Centre, The Hive Creativity & Arts Centre, Food and Nutrition block and, off site at Long Wittenham, our first ever Boathouse, allowing the extra-curricular programme to be continually expanded and enriched.
One of Caroline’s particular strengths has been in identifying, recruiting and developing skilled members of staff and enabling them to take on significant positions of leadership. During her career, 10 members of staff nurtured and mentored by Caroline have gone on to headships elsewhere with an 11th taking up post in September.
Caroline was President of the Girls’ Schools Association in 2016 having previously been Chair of its Education Committee and sat on the GSA/HMC Universities Committee for six years. She was Vice-Chair of the Independent Schools’ Council between 2017 and 2020 and has been a board member of the Independent Schools Examinations Board and an ISI inspector.
Mrs Carol Oster Warriner, Chair of Governors said: “Caroline is one of the most inspirational leaders in UK education, with an exceptional record of national leadership through her work with the Girls’ Schools Association and the Independent Schools Council. During her 15 years at Headington, she has combined strategic vision with courage, compassion and an unwavering commitment to pupils and staff, most recently guiding our landmark merger with remarkable clarity and humanity. We are immensely proud to have her as our Head.
“Her Tatler Lifetime Achievement shortlisting, alongside the School’s selection as a finalist for Regional Independent School of the Year: South, is a fitting and well-deserved reflection of her exceptional leadership.”