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Drew Hollenback has a diverse work experience with a focus on software development and management roles. Drew started their career at 365 MEDIA SOLUTIONS as a Marketing Coordinator and Assistant Manager from March 2007 to January 2008. Drew then joined U-Haul International, Inc in May 2008 as a Reservation Manager until May 2009, and later worked as a Rate Analyst from June 2009 to October 2010. Drew moved up the ranks and served as an Operations Program Manager from November 2010 to April 2013, and then took on the role of Application Development & Support Manager from April 2013 to August 2018. Most recently, they have worked as a Front-End Software Developer from August 2018 to June 2020, and is currently working at U-Haul International, Inc as a Lead Software Developer from June 2020.

Drew Hollenback earned a Bachelor of Science degree in Marketing from the University of Arizona between 2005 and 2009. Later, between 2016 and 2017, Drew attended Bloc to complete a Full-Stack Web Development program.