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Giancarlo DiMascio has a diverse work experience in the golf industry. Giancarlo started their career as a caddie and worked in Golf Operations at Oak Hill Country Club from August 2012 to October 2015. During this time, they also worked as a Marketing Specialist and Marketing Representative at Sheraton Hotels & Resorts from January 2016 to April 2017. In 2016, Giancarlo worked as a self-employed Professional Golfer from July 2016 to January 2018. Giancarlo then gained experience as a Traveling Intern at the American Junior Golf Association from March 2018 to June 2018. Giancarlo further enhanced their golf expertise by working as an Assistant Golf Professional at Monroe County from June 2018 onwards. In 2019, they joined the United States Golf Association and Pebble Beach Resorts, focusing on Championship Operations and Communications and U.S. Open Operations and Communications, respectively. In 2020, Giancarlo worked as a PGA Championship Assistant for the PGA of America from April to August.

Giancarlo DiMascio has a Bachelor's degree from Rochester Institute of Technology. Giancarlo also holds a Master's degree from Duke University - The Fuqua School of Business and another Master's degree from Rochester Institute of Technology. Additionally, Giancarlo has attended Northeastern University and Monroe Community College, though the specific degree or field of study for these institutions is unknown.