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Harry Milton has a diverse work experience that spans over many years. Harry started their career as a Junior Accountant at Lovewell Blake in 2006 and worked there until 2008. Harry then gained some work experience in the press office of Ipswich Town FC in 2010. In 2011, Harry worked as a Media and Journalism Career Intern at the University of Leeds. Harry joined Chatter Communications in 2013 as an Account Executive and later worked their way up to become an Account Manager in 2015 and then a Project Manager in 2018. Currently, they hold the position of Head of Project Management at Chatter Communications, starting in May 2022.

Harry Milton attended City College Norwich from 2007 to 2009, where they completed A Levels in History, English, and Law. From 2009 to 2012, they furthered their education at the University of Leeds, earning a Bachelor of Arts (B.A.) degree in History.