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Anna Whiteley has a long and varied work experience, beginning in 2004 with a role as an Out of School Care Supervisor at THE GRANGE PARTNERSHIP LIMITED. In 2006, they became a Teaching Assistant at New Park Community Primary School in Harrogate. In 2007, Anna moved to Grove Road Community Primary School, where they worked as a Higher Level Teaching Assistant for seven years. In 2013, Anna began working at Pobble Education as the Head of Marketing, where they grew the company's social following from zero to 40K+ followers. In 2018, Anna became an Owner and Freelance Social Media Consultant at Sway Social, a SEND Digital Consultant at ANITA DEVI LTD, and a Freelance Consultant at Teach Active. In 2019, Anna took on a role as a Freelance Consultant at Sporting Influence.

Anna Whiteley's education history includes a BA (Hons) in Childhood Studies from Leeds Beckett University, which they completed between 2000-2004. Anna also attended St Aidan's C of E High School between 1990-1997, where they studied Media Studies, English Literature, English Language, and Sports Studies. In addition, Anna has obtained several certifications, including a CACHE Level 2 Certificate in Understanding Mental Health First Aid and Mental Health Advocacy in the Workplace (2021), a Cognitive Behaviour Therapy (CBT) Diploma (2021), a Fundamentals of Digital Marketing certification from Google (2019), a Diploma in Social Media Marketing and a Social Networking and Viral Marketing Using Facebook certification from Alison (2016), and certifications in Inbound Marketing, Social Media Marketing, Email Marketing, and HubSpot Marketing Software from HubSpot Academy (2020).