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Benjamin Orr has extensive work experience in the insurance and sales industry. Benjamin started their career at HD Supply in 2005 as an Outside Sales Representative, where they worked until 2010. From 2010 to 2014, they worked at ST. REGIS CULVERT, INC as an Outside Sales Representative. In 2014, they joined Sentry as an Account Manager and remained in that role until 2020. Currently, they are working as a Commercial Insurance Agent at Shepherd Insurance.

Benjamin Orr obtained a Bachelor's degree from Purdue University, where they attended from 2000 to 2004. Prior to that, they completed their high school education and received a diploma from Brebeuf Jesuit Preparatory School between 1996 and 2000.