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Matt Pickersgill has had a diverse range of work experiences throughout their career. Matt started as an Internal Auditor at Saga Group Ltd., where they later transitioned to roles as a Management Accountant and Commercial Accountant. Matt then moved on to Trek Bicycle, where they initially worked as an Internal Account Manager before taking on the role of a Management Accountant. Matt later became the Ascend UK (EPOS) Business Manager, responsible for launching and developing the Ascend software application in the UK market. Matt then became the UK Dealer Services Manager, where they focused on continuous improvement and financial benchmarking for independent customers. Matt then took on the position of European Financial Services Manager, where they oversaw operations and financial involvement for three UK owned stores. Finally, they became the European Retail Operations Manager at Trek Bicycle, responsible for all operational processes and procedures in their stores across Europe, along with the acquisition and onboarding of businesses at different stages of development.

Matt Pickersgill began their education at Bradford Grammar School in 1987, where they studied until 1994. Matt then went on to attend the University of Birmingham from 1994 to 1997, where they earned a degree in Geography. After completing their undergraduate studies, Matt pursued further education at The Chartered Institute of Management Accountants from 2000 to 2006, where they attained the CGMA qualification.