Leo Winkley

Leo has been Headmaster of Shrewsbury School since 2018. The Shewsy was founded by teachers from Shrewsbury School in 1903. As Headmaster, Leo has been active in deepening the historic links between the school and the Shewsy. He has over 30 years’ experience of leading in independent boarding schools including previous roles as Headmaster of St Peter’s York (2010-2018) and Deputy Head of Bedales School (2004-2010). He was Chair of the Boarding Schools Association, which represents state and independent schools, in 2017.

As a trustee, Leo contributes his skills in leading the Board of Trustees and working closely with the Shewsy’s CEO to help guide the charity’s governance and strategy. He is particularly passionate about community outreach and partnerships. In 2021, he co-founded a national charity for advancing cross-sector educational partnerships, The School Partnerships Alliance.

Outside of work, Leo enjoys a broad range of sports and spending time with his family, as well as gentler pursuits such as watercolour painting. He has raised funds for various national charities and volunteers at a local food bank.