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Ashley R. Gillespie has a diverse work experience in various industries. Ashley R. started their career in 2007 as a Broker's Assistant at Nasser Real Estate, Inc and then worked as a Leasing Consultant at Morgan Properties from 2005 to 2010. In 2010, they became an ESL Teacher at Chungdahm Learning. Ashley joined ADP in 2011 as a District Manager for Small Business Services before transitioning to Tactix Real Estate Advisors, LLC in 2012 as a Commercial Real Estate Broker. Ashley R. then moved on to The HOW Group in 2013, where they held multiple roles including Property Manager, Director of Property Management, and currently serves as the VP of Strategical Development and Building Enhancements.

Ashley R. Gillespie received a Bachelor's degree in Marketing and International Business from the University of Scranton, where they studied from 2005 to 2009. In 2007, they also attended Universidad Pablo de Olavide for a period of time, studying International Business. However, no specific degree was mentioned for their education at this institution.