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Jeffrey Watson has a diverse work experience spanning over two decades. Jeffrey began their career in the United States Marine Corps, serving as Infantry from July 1996 to September 2002. Jeffrey then moved on to CSX Transportation, where they started as a Management Trainee in January 2002 and eventually became Roadmaster before leaving the company in May 2008. Since then, Jeffrey has worked at Genesee & Wyoming Inc. In this organization, they have held various positions, including General Manager Maintenance of Way, Vice President Southern Region Engineering, General Manager Track & Infrastructure, and currently, they serve as the Vice President of Engineering, a role they have held since April 2020.

From 1996 to 2000, Jeffrey Watson attended Mississippi State University, where they earned a Bachelor's degree in Agricultural Engineering.