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Diana Villegas has worked in a variety of roles in the sales and marketing industry since 2003. Diana began their career at State Farm Insurance as an Office/Sales Manager, where they coordinated and developed methods and procedures to increase sales, lower costs, and obtain greater efficiency. From 2009 to 2011, they worked at Nova Driving School as a Sales Manager, where they enforced, incorporated, and monitored quality levels, up-to-date inspections, and vehicle performance. In 2011, they moved to Trans Chicago Limousine as an Operation Manager, where they developed, planned, directed, and coordinated logistical procedures for transportation services for corporate meetings and trade shows. From 2016 to 2019, they worked at ISSA - The Worldwide Cleaning Industry Association, where they held several roles including Associate Director - Latin America, Senior Manager - Latin America, Industry Outreach Manager - Latin America, and International Membership Specialist. In 2019, they returned to Nova Driving School as the Director of Sales Marketing.

Diana Villegas completed their Bachelor of Science in Business (BS) from DePaul University in 2014, with a major in Business Administration and Management, General. Diana had previously earned an Associate of Arts (A.A.) from City Colleges of Chicago-Wilbur Wright College in 2010, also with a major in Business Administration and Management, General.