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Anna Headley has a diverse work experience spanning multiple roles and industries. Anna started their career as a Staff Registered Nurse at Sue Ryder in 1993 and worked there until 2001. Anna then joined York Teaching Hospital NHS Foundation Trust as a Senior Staff Nurse from 2001 to 2003. Anna then worked at Nuffield Health as an Inpatient Services Manager from 2003 to 2008, where they managed various specialized medical units. Anna then joined The Disabilities Trust in 2008 and held several positions, including Service Manager, Divisional Operations Manager, and Director of Autism, Learning Disability, and Education. Anna worked at DISC as an Operations Director from 2016 to 2017. Anna'smost recent position is with Humankind Charity, where they served as the Executive Director of Operations South, West Yorkshire and North West from 2017 to 2022, and currently holds the position of Executive Director of Clinical Quality and Performance starting from February 2022.

Anna Headley received their Master of Psychology degree from the University of Sunderland from 2020 to 2022. Prior to that, they obtained a BSc (Hons) in Professional Studies in healthcare from The University of Huddersfield between 1999 and 2004. Additionally, they attended Tadcaster Grammar School from 1982 to 1987, but no degree or field of study is mentioned for this period.