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Dwight Houseman has held a variety of roles since 2010. Dwight began their career as a Traffic Director for Jaflo Tree Inc. in 2010. In 2011, they held an internship with the PA State District 118 House of Representatives. From 2014 to 2018, they worked as a Seasonal Employee for HH Gregg Electronics, a Landscaping for Evergreen Landscaping, an Assistant Baseball Coach for Taylor Legion, an Amateur Scout for the World Amateur Baseball Series, and a Baseball Operations Internship for Perfect Game Baseball Softball. In 2018, they were a Delivery Driver for FedEx and a Sales Representative for Dvinci Energy.

Dwight Houseman earned a Bachelor's Degree in Sport and Recreational Management from St. Andrews University between 2013 and 2015.