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Derrick Woolfson has a diverse work experience spanning over several years. Derrick began their career as a Head Resident Assistant at McDaniel College in 2010, where they stayed until 2012. Following that, they joined Younger AutoGroup as a Business Development Manager, working there from 2012 to 2018. In 2018, they transitioned to Beltway Companies, where they currently hold the position of Vice President of Business Development.

Derrick Woolfson completed their Bachelor of Arts degree in Philosophy from McDaniel College, where they studied from 2008 to 2012.