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Simon Holdsworth started their work experience in 1995 as a Solicitor at Macfarlane Guy, where they worked until 1997. In 1997, they joined Thrings as the Managing Partner. In this role, they are responsible for managing the legal and operational side of the business. Simon also works closely with Heads of Department and Offices, individual partners, and Operation Directors to shape the firm to meet the changing expectations of clients in the legal market.

Simon Holdsworth attended Wellsway Secondary School in Keynsham. After completing their secondary education, they enrolled at Oxford Brookes University. Following their time at Oxford Brookes, they attended the College of Law in York. Specific details about degrees earned or fields of study are not provided.