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Kyle Calhoon has a diverse work experience in the sports industry. Kyle started their career in 2005 as an Assistant Groundskeeper at Lake County Captains. Kyle then joined the Cleveland Browns in 2005 as a Groundskeeper, where they worked until 2010. In 2008, they also worked as a Groundskeeper for the Cleveland Indians. From 2010 to 2012, Kyle served as the Head Groundskeeper at MetLife Stadium, responsible for maintaining the synthetic playing field for various events. Kyle then joined the New York Yankees as a Groundskeeper from 2012 to 2014. Kyle continued to expand their expertise by working as the Grounds Manager for the San Francisco 49ers from 2014 to 2015. Currently, they hold the position of Executive Director Ballpark Operations at Hartford Yard Goats Baseball, starting in 2022. Additionally, Kyle has also been the Sports Turf Manager at Hartford Yard Goats Baseball since 2015.

Kyle Calhoon attended Penn State University from 2013 to 2014, where they obtained a Certificate in Turf and Turfgrass Management. Prior to that, from 2005 to 2009, they studied at Walsh University, earning a degree in General Studies with a focus on Business Administration and Management. Kyle also holds a Bachelor of Arts degree in General Studies from Walsh University, although the specific years of attendance are not provided.