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Shawn Bailey has a varied work experience. From 2001 to 2005, they worked as a Sales Associate at Sunglass Hut and a District Associate at AT&T. From 2003 to 2006, they were a Staff Writer at Skinnie Magazine and a Sr. Account Manager | UI/UX Lead at FatTail, Inc. At FatTail, Inc., they worked directly with clients and internal teams to implement and integrate AdBook in daily usage with the largest publishers in the online space. Shawn also helped spearhead a complete UI overhaul and redesign process for system modernization, provided specs and detailed mockups for new pages and tools, and wrote the company's design guidelines and best practices for all new pages and controls. Additionally, they evaluated client needs and assisted the development and QA teams. Shawn had extensive usage and knowledge of DFP and OAS ad servers, as well as working knowledge of Salesforce and the AdBook system.

Shawn Bailey obtained a Bachelor's Degree in Marketing from the University of La Verne in 2003, following a period of study from 1999 to 2003. In 2004, they began a Master of Business Administration (M.B.A.) program at the University of La Verne, which they completed in 2006 with a focus on Leadership and Management. In 2021, they obtained a User Experience Design certification from General Assembly.