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Graham Caywood has a diverse work experience spanning various industries and roles. Graham began their career as a Corporate Security Intern at Wm. Wrigley Jr. Company in 2007, where they contributed to the revision and organization of a new corporate security manual. In 2008, they joined Numerator Management as an Assistant Manager. In 2009, they joined the Aidmatrix Foundation as a Marketing Intern and later became a Program Specialist, working in multiple facets of the nonprofit organization. In 2015, Caywood worked as a Team Lead for MBA+ Strategy Project at Texas Instruments. Graham then joined AT&T in 2016 as an Associate Public Relations Consultant. Caywood co-founded Actionfigure (formerly TransitScreen) in 2013, a transportation software and digital signage company. At Actionfigure, they served as the Co-Founder and Communications Director. In 2017, they joined Dell Technologies as a Senior Advisor in Product Management and later transitioned to roles in Product Marketing and Market Analytics & Business Strategy. Caywood's most recent role at Dell Technologies is as a Consultant in Market Analytics & Business Strategy.

Graham Caywood pursued their education in a chronological order, beginning with their bachelor's degree at UCLA from 2004 to 2008. During this time, they focused their studies on psychology. Subsequently, Graham enrolled at the Texas McCombs School of Business, where they pursued a Master of Business Administration (M.B.A.) degree from 2015 to 2017. Throughout their M.B.A. program, they specialized in high tech marketing.