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Hillary Jacobson has worked in a variety of roles over the past two decades. Hillary began their career in 2001 as a Stable Attendant/Draft Horse Driver at Disneyland. In 2002, they took on a Photo Assistant role at Jay Allen Photography. From 2008 to 2011, they worked as an Office Administrator for Standards of Excellence. Hillary then moved on to PIRCH as Manager of Joy Fulfillment from 2011 to 2015. In 2017, they became an Operations Manager at Chef'd, and in 2018 they were hired as a Cash Risk Manager at KushCo Holdings, Inc.

Hillary Jacobson attended Golden West College from 2005 to 2008, where they earned an Associate of Arts (AA) degree in Design and Applied Arts.