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Joseph Benson has a diverse work experience, starting as a Bartender/Promotions at McFaddens Saloon from June 2000 to December 2003. Joseph then joined Len Stoler Lexus as a Sales Manager from February 2004 to April 2014. Following that, Joseph worked at Len Stoler Audi & Porsche as a General Sales Manager from May 2014 to April 2015. Joseph then transitioned to Lexus of Towson as a Finance Manager from April 2015 to March 2017. Currently, Joseph is the Finance Director at Len Stoler Automotive Group starting from March 2017.

Joseph Benson attended Baldwin Senior High School from 1996 to 1999. Joseph then pursued a Bachelor's degree in Sports Management & Business from Towson University from 1999 to 2003.