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Richard Diamond has a diverse work experience spanning over several roles and industries. Richard began their career in 1993 as an Information Officer at the Robert Jones & Agnes Hunt Orthopaedic & District Hospital NHS Trust, where they were involved in administrative and clinical information analysis and database design. In 1998, Richard moved on to become the Operations Director at Independent Computer Systems Ltd until 2007. Richard then became the Managing Director at Olio e Farina from 2007 to 2011. Richard diversified their skills by taking on roles in project management and business development at Richard Diamond in 2011. In 2012, they joined One to One (North West) Ltd as the Head of IT, also serving as the Acting COO from January 2019. Richard joined Xyenta in 2019, first as the Lead Technical Analyst and later as the Head of Delivery starting in January 2021.

Richard Diamond attended Sir John Talbots School Whitchurch from 1983 to 1991. During their time there, they completed A Levels, Business Administration NVQ Level 3 (equivalent to 2 A Levels), and GCSEs. No specific degree was mentioned.