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Jenny Holaday has a diverse and extensive work experience in the gaming and marketing industry. Jenny started their career at Harrah's AC Region in 2003 as the VP of Marketing, where they managed various marketing functions and implemented key strategies for the region. In 2007, they became a Marketing Consultant at Holaday Marketing before moving on to MotorCity Casino-Hotel in 2010. At MotorCity Casino-Hotel, they served as the SVP of Operations and later as the SVP of Marketing. In 2016, they returned to Holaday Marketing as a Marketing and Operations Consultant with senior-level executive expertise. Jenny then joined DailyFuel in 2017 as President before taking on the role of EVP Operations at Encore Boston Harbor in 2019. Currently, they serve as the President of Encore Boston Harbor.

Jenny Holaday attended the University of Nevada, Reno from 1986 to 1989. During their time there, they pursued a degree in English, with a focus on writing, communications, and literature.