Caroline Jordan, head of Headington Rye Oxford, has been named the winner of the Lifetime Achievement Award at the Tatler Schools Awards, recognising her contribution to education over a career spanning more than 30 years.
Mrs Jordan has led Headington since 2011 after serving as headmistress of St George’s School in Ascot.
Dr Stephen Burley, who was named a Tatler ‘Best Head’ in 2025, will succeed her as head in September 2027.
Dr Stephen Burley, who was named a Tatler ‘Best Head’ in 2025, will succeed her as head in September 2027. (Image: Headington Rye Oxford)
Reacting to the award, she said: “I am absolutely thrilled. This is such an accolade to the amazing support I have had from the girls, staff and parents that I have had the huge pleasure to work with over the last 30 years.
“I will truly miss the warm and ambitious communities I have found in girls’ schools and will continue to watch them with great affection when I retire next summer. For now, I am going to enjoy every moment.”
She credited her nomination to those she had worked with, including colleagues, family and all the “amazing thousands of girls” who have been through the schools she’s worked in.
“It’s a tribute to them”, she said, adding: “That’s what really makes a difference to me.”
Educated at St Helen and St Katharine School in Abingdon and later the University of Oxford for geology, Mrs Jordan spent around a decade in the commercial sector. In 1994 she retrained as a teacher while juggling her three-month-old baby at home.
During more than 22 years in headship, she has become a prominent voice in girls’ education and a passionate advocate for encouraging young women into science, technology, engineering and mathematics (STEM) subjects.
Her time at Headington has seen some of the most significant developments in the school’s history, including its merger with Rye St Antony in 2024 to create Headington Rye Oxford.
Under her leadership, the school has also expanded its academic and co-curricular offering and invested in facilities including a new Dance and Fitness Centre, library, sixth form centre, The Hive Creativity & Arts Centre, food and nutrition block, and a boathouse at Long Wittenham.
Other achievements include mentoring 10 people to become headteachers, serving as president of the Girls’ Schools Association in 2016, being vice-chair of the Independent Schools’ Council between 2017 and 2020 and holding positions with the Independent Schools Examinations Board and the Independent Schools Inspectorate.
Caroline Jordan, headteacher at Headington Rye Oxford, said she is “thrilled” with the award (Image: Headington Rye Oxford)
The school said a programme of events and activities will take place throughout the next academic year, allowing current and former pupils, parents and staff to celebrate Mrs Jordan’s contribution before her retirement.
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.”
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