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Derrick Free has worked in various positions since 1999. Derrick began their career as Manager of Government Programs at the Nashville Area Chamber of Commerce in 1999. In 2006, they took on the role of Attorney at Farrar and Bates, LLP. In 2010, they became a Financial Advisor at Northwestern Mutual. In 2014, they moved to Lipscomb University as Director of Corporate and Foundation Relations. In 2018, they returned to Northwestern Mutual as Chief Operating Officer (COO). Most recently, in 2019, they took on the role of Executive Vice President and General Counsel at Gray Line Tennessee.

Derrick Free obtained their J.D. Cum Laude from the University of Tennessee College of Law between 2001 and 2004. Prior to this, they completed a B.A. in Political Science at Lipscomb University between 1994 and 1998.