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Aileen Cowler has a diverse work experience spanning multiple companies and roles. Aileen began their career in 1997 at Card Protection Plan (CPP) as an Operations Trainer and Coach, where they stayed until 2005. In 2008, they joined NFU Mutual as an L&D Specialist and later transitioned to a Talent Development Specialist role, which they held until 2022. Aileen then moved on to Isio in 2022, where they currently serve as a Talent Development Manager.

Aileen Cowler attended Newcastle College from 1999 to 2002, where they obtained a Higher National Diploma (HND) in Technical Theatre/Theatre Design and Technology. In 2017, they also obtained a certification in Talent Management from the Chartered Institute of Personnel and Development (CIPD). Aileen Cowler has mentioned a CIPD Diploma, but no further details or information about the institution, month or year of its acquisition is available.