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Richard Dearing has a diverse range of work experience. Richard started their career as a Trainee Draughtsman at Mabey Bridge Limited in 1983. Richard then worked as a Retail Planner/Designer at Hallmark Cards from 1985 to 1989. From 1989 to 1990, they were a Sales Engineer at Integrated Vision Systems Limited. Richard then joined Autodesk and worked as a Technical Support Specialist from 1990 to 1992, and as a Technical Co-ordinator Events from 1992 to 1995. From 1995 to 1997, they served as a Technical Support Manager at Traxdata Limited. Richard then joined CD Team Limited, where they held various roles including Technical Support Manager, Technical Director, and Operations Director. In 2012, they took a career break to be a Full-Time Parent and also volunteered as a Parent Governor. Richard later worked as an Operations Consultant at Intelligent Retail for a brief period. Since 2014, Richard has been associated with CitNOW Video, where they served as the Head of Operations and later as the Head of Salesforce Development.

Richard Dearing's education history includes attending Reading Technical College from 1982 to 1985, where they obtained a BTEC National Certificate in Civil Engineering. Additionally, from 1982 to 1983, they pursued a Mechanical Engineering Apprentice program at the Engineering Industry Training Board.

In terms of certifications, Richard obtained the Salesforce CPQ Reference Data Deployment Certification from Prodly in May 2019. Richard also completed Salesforce Trailhead training in October 2017. In May 2015, Richard obtained the ITIL® Foundation certificate in IT Service Management from AXELOS Global Best Practice. Furthermore, in December 2013, they obtained both the PRINCE2® Foundation and PRINCE2® Registered Practitioner certifications from APMG-International.