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Dean Whitehead has a diverse work experience in the field of technology. Dean began their career as a Server Administrator at Unisys in 1995 and then moved on to become an NT Technical Consultant at Sheridan Systems Ltd from 1995 to 1998. Following this, they worked as a Senior Network Administrator at Huntleigh Healthcare Ltd from 1998 to 2000. From 2000 to 2006, Dean served as the Help Desk Manager and Senior Technical Support at Pericom Plc. In 1999, they founded Verticality and held the position of IT Director there. In 2005, they founded EasyWeb Recruitment, where they functioned as both Founder and IT Director. Most recently, Dean has been working at Bluecube Technology Solutions as a Technical Consultant since 2006 and later took on the role of Chief Technology Officer in April 2019.

Dean Whitehead attended Sir Frank Markham School from 1991 to 1993. Following that, they enrolled in Wolverton College from 1993 to 1995, where they pursued a BTEC Diploma in Electrical Engineering.