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Thomas Matthewman has a diverse work experience in various roles and industries. Thomas started as a Teachers Assistant at Brockhurst & Marlestone inc. from September 2010 to June 2011. Thomas then worked as a Marketing Representative at the Department of Ancient History UoB. from February 2014 to March 2014, where they represented the department to prospective students. Thomas gained legal and commercial experience while shadowing senior management at Paynet Group & Pesa Point Kenya in June 2014. Thomas also worked as a Shadowing Programme Manager at The Law & Development Partnership in September 2014, conducting research on baseline economic figures for developing countries. Thomas joined Pen Underwriting UK as a Secondee Claims Handler from June 2018 to September 2018, followed by roles as Associate and Trainee Solicitor at Mills & Reeve from September 2016 to September 2021. Thomas worked as a Senior Claims Handler at Kennedys from September 2021 to January 2022. Thomas was then appointed as a Claims Manager at Pen Underwriting UK from January 2022 to June 2023, before being promoted as the Head of Financial Lines and Specialty Claims in June 2023.

Thomas Matthewman attended Pangbourne College from 2008 to 2010. Thomas then pursued a Bachelor's Degree in Ancient History at the University of Birmingham from 2011 to 2014. From 2014 to 2016, they studied Law at the University of Law, completing a GDL, LPC, and Business MSC.