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Andy Aiken has a diverse work experience spanning different industries. Andy began their career in the military, serving as a Captain and Military Intelligence Officer in Iraq and South Korea. After their service, they worked as a Summer Associate at Credit Suisse. Andy then joined Peter J. Solomon Company as an Associate Director before moving to Fast Retailing as a Senior Director of Business Administration. Most recently, they held roles at Theory, including Senior Director of Business Strategy, Vice President of E-Commerce and Business Strategy, and Chief Operating Officer for Theory UK/EU.

Andy Aiken obtained a BSc degree in History and Systems Engineering from the United States Military Academy at West Point, where they studied from 2001 to 2005. Following that, they attended Harvard Business School from 2010 to 2012 and received a Master of Business Administration (MBA) degree.