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Diana Midson has a diverse work experience. Diana began their career in 2000 as a Senior IT Recruitment Executive for Computer People, where they quickly progressed to a full recruitment life-cycle and new business development role. Diana then worked as a Key Account Manager for BIC from 2003 to 2004 and as a Corporate Client Manager for Bupa from 2004 to 2006. From 2006 to 2012, they served as a Senior Corporate Account Manager for PruHealth, managing a portfolio of top corporate clients in various industries and ensuring customer satisfaction. Diana then worked as an Associate Director for Morgan Keating Ltd in 2012 before joining Nuffield Health as an Account Director, Corporate Wellbeing, from 2013 to 2014. Following this, they took time off to be a full-time mother. Most recently, they have been serving as a Business Development Manager for Ranpak since 2016.

Diana Midson completed their A-levels in French, German, and Classics from Queen Margaret's School, Escrick between 1988 and 1995. Diana then pursued a Bachelor of Arts with Honors degree in French and Classics at the University of Leeds from 1995 to 1999. During their undergraduate studies, Diana also attended Université Paris-Sorbonne for French language studies from 1997 to 1998.