Senior leadership

Mr Stephen Jeffries
Chief Executive, Leicester Grammar School Trust

Stephen leads the Trust strategically as the principal officer. He chairs the Executive Committee, working with the Heads of the three schools to ensure pupil wellbeing, personal development and educational achievement are at the heart of every decision.

Stephen has lived almost his entire life in the East Midlands and the last 25 years in Leicestershire. Educated at Nottingham High School, he went on to read Law at the University of Leeds.

Stephen trained as a Chartered Accountant with EY, and spent a further decade at KPMG and PwC in their Midlands practices. Following this, he held a senior finance role in a FTSE 100 company before serving as a Finance Director for eight years in the Financial Services sector.

Stephen joined the Trust in 2019 as Director of Finance and Operations. He brought extensive experience in directing the Trust’s financial, operational and compliance functions, including legal, HR, IT, and data protection. He also serves as Director and Chair of LGS Enterprises, the Trust’s trading subsidiary.

Stephen is a keen pianist and is passionate about sport. While he may no longer be the champion sprinter from his school days, he enjoys playing squash regularly and is a season ticket holder at Nottingham Forest. He is immensely proud of his two sons, both of whom were educated within the Trust. 

Mrs Christina McCullough
Headmistress

Christina joined the Leicester Grammar School Trust in September 2023 from The Kinglsey School, Leamington Spa where she was in post as Senior Deputy Head and previously Acting Head and Pastoral Deputy.

She began her career at Princethorpe College, Rugby teaching PE and Geography and she enjoyed being part of the wider pastoral life of the school.

Christina loves to travel and is passionate about pupils taking part in the co-curricular life of the school.

Mrs Lindsey Ashwin
Deputy Head [Academic]

Lindsey joined the Trust as Director of Music at Stoneygate School in 2013. She has since taken on a number of roles, including Head of Senior School and Exams Officer. As Deputy Head (Academic) since 2022, Lindsey is responsible for the academic outcomes of pupils, working closely with the teaching body. She writes the timetable, manages exams and curriculum and collaborates with colleagues for the best outcomes of all pupils. She teaches Music across the school, from Reception to Year 11 and loves the variety of this role. 

Lindsey graduated from The University of Birmingham with a degree in Music. Her passion for education and developing her knowledge of successful organisations led her to take on an MBA from Coventry University, which she achieved with distinction. She has since passed the National Professional Qualification for Headship (NPQH). When not in school, Lindsey enjoys singing in choirs and as a soloist.

Miss Kate Wooldridge
Deputy Head [Pastoral]

Kate joined the Trust in September 2025, bringing a breadth of experience from roles as Director of Sport and Assistant Principal across international, state, and independent schools.

Alongside her professional career, Kate has represented England Masters Hockey, captaining the Over-35s team for the past three years. She is also a qualified Personal Trainer with a lifelong passion for sport, fitness, and inspiring others to lead active, healthy lives.