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Gaynor Bailey has a diverse work experience in the finance and recruitment sectors. Gaynor started their career at the Children's Food Trust in 2009 as a Finance Assistant, where they witnessed significant changes due to government cuts, leading to the organization transitioning into a charity. In 2014, Gaynor joined Sewell Wallis as a Finance Assistant and later became a Senior Finance Consultant, specializing in senior interim and permanent finance recruitment. In 2019, they moved to the Nexus Multi Academy Trust, initially working as a Purchase to Pay Officer, then as a Corporate Finance Officer, and currently holds the position of Transactional Finance Team Leader.

Gaynor Bailey attended the Birley School from an unknown start year until 1998. No degree or field of study information was provided.