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Charles Littlefield has a diverse work experience spanning various roles and companies. Starting in 2003, they worked at Diageo as a Manager in Metro New York for three years. From 2007-2008, they were an Associate Brand Manager at Frito Lay. Charles then moved on to Unilever as an Associate Brand Manager before joining E. & J. Gallo Winery as a Marketing Manager in 2008. At Bacardi, Charles held multiple positions including Senior Brand Manager, Director of Customer Marketing, and Director of Commercial Planning and Activation. From 2016-2018, they worked at HEINEKEN as the General Manager of Five Points Trading Company. Most recently, Charles has been with Mast-Jägermeister US, Inc. where they started as the Senior Director of Brand Marketing before being promoted to Vice President of Brand Marketing in December 2019.

Charles Littlefield attended Middlesex School for an unspecified amount of time, where they did not receive a degree. Charles then went on to study at Cornell University from 1998 to 2002, earning a Bachelor's degree in Industrial and Labor Relations. Later, from 2006 to 2008, they pursued a Master of Business Administration (MBA) degree from the University of Virginia Darden School of Business.