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Tom Gregg has worked in the auto industry since 1997, starting as a Sales Associate/Internet Sales at Anderson Motor Company. In 2002, they moved to Metro Toyota as a Sales Manager/Finance Manager, where they established an exclusive internet process and was promoted to New Car Sales Manager at the age of 21. In 2005, they transferred to Elgin Toyota as Used Car Manager/Finance Manager, and in 2007 they moved to Pauly Toyota as Used Car Manager. During their time at the Dan Wolf Automotive dealerships, they were the Internet Director at Toyota of Naperville from 2011 to 2013 and led both sales and service BDCs. In 2013, they founded and became the CEO of Vehicle Acquisition Network (VAN), a company that helps dealers acquire private party vehicles more affordably, efficiently and effectively.

Tom Gregg obtained a Bachelor of Applied Science (B.A.Sc.) in Business from Northeastern Illinois University between 2006 and 2009. Prior to that, they earned an Associate of Science (A.S.) in Business Administration and Management, General from McHenry County College.