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James O'Shaughnessy has a comprehensive work experience in various roles and industries. James started in 2004 as a Project Manager at Label Link before becoming an Account Manager at Poulters, where they managed the coordination and production of press advertising for William Hill. In 2008, they worked as a Freelance Senior Account Manager across multiple companies and gained experience in packaging design and radio advertising. From 2010 to 2014, they served as the Head of Client Operations at Words&Pictures, overseeing all client operations and developing internal communication solutions. James then joined Jaywing in 2015 as an Account Director, where they established and strengthened key client relationships. In 2017, they became the Head of Client Services at Fox Agency, managing major clients and contributing to the agency's growth. From 2018 to 2020, they served as a Director at black&blue agency, focusing on client service and creativity. Currently, they hold the position of Account Director at Dragon Rouge, and starting in 2021, they will take on the role of Client Director at FutureBrand.

James O'Shaughnessy attended Harrogate Grammar School from 1991 to 1998, where they did not pursue any specific degree or field of study. Following this, they attended Leeds Beckett University from 1999 to 2003, earning a Bachelor of Science (BSc) degree with a 2:1 in Business Information Management.