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Gary Probert has extensive work experience in the football industry. Most recently, they served as the Director of Football Operations at Ipswich Town FC starting in November 2021. Previously, they worked at Bristol City Football Club for several years, holding various roles including Academy Manager, Assistant Academy Manager, Professional Development Phase Coach, and Lead Phase Coach. Prior to that, they worked at The Football Association as an FA Licensed Tutor from December 2009 to August 2016. Gary also worked at Gloucestershire FA as the County Development Manager from August 2007 to March 2013, and at Forest Green Rovers Football Club as the Youth Development Manager & FE Academy Manager from August 2005 to August 2007.

Gary Probert received a Bachelor of Science (BSc) in Sports Coaching from the University of Wales Institute Cardiff in the years 2002 to 2005. Gary later acquired a PGCert in Football Academy Management from the University of Portsmouth in 2020 to 2021, as well as a Diploma in Professional Studies in Football Management from the University of Liverpool during the same period. Additionally, Gary holds certifications such as the EMCC Mentor qualification from EMCC Global and the FA Advanced Youth Award and UEFA A Licence from The Football Association.