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James Matthews has a diverse work experience spanning several roles in different companies. James started their career in 2004 as an AppleCare Support at twenty4help, where they provided assistance to customers. In 2006, James joined Anchor Trust as a Service Desk Technician, and later advanced to the role of Senior Service Desk Technician. During their time at Anchor Trust, they were involved in various responsibilities, including the development and support of Service-Now and CACI OfficeBase, as well as the development of custom applications using the Service-Now platform. James also worked on supporting and developing the Northgate product, specifically in the areas of Repairs and Service contracts. In 2018, James joined Oak Engage as a DevOps Engineer.

James Matthews attended Northumbria University from 1999 to 2003, where they pursued a degree in Computing Studies.