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John Whittle's work experience began in 2000 with the Caudwell Group, where they participated in their Graduate Program until 2003. John then joined Phones 4u, starting in September 2000 and working in various financial and commercial roles until January 2008. From January 2008 to November 2013, John held positions of increasing responsibility at Phones 4u, including Associate Commercial & Trading Director, Director of Trading, Director of Commercial, and Chief Commercial Officer. In 2015, John co-founded UNSHACKLED.com, a company focused on disrupting the traditional retail mobile model, where they currently serve as CEO.

John Whittle's education history begins with their high school education at Queen Elizabeth's Grammar School in Blackburn from 1987 to 1997. John then pursued a Bachelor's Degree in Economics at the University of Wales Aberystwyth from 1997 to 2000. After completing their undergraduate studies, they obtained a Chartered Institute Management Accountants (CIMA) certification from 2000 to 2002. Lastly, in 2014 to 2016, John Whittle received FCA Approved Person education, earning an FCA degree. No field of study was specified for the CIMA and FCA education.