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Jonathan Charles currently serves as the Director of Football Operations for Massachusetts Pirates, LLC, leading the team's operational strategies and activities since March 2021, culminating in an Indoor Football League Championship in 2021. Prior experience includes a role as Regional Store Manager at Extra Space Storage, where Jonathan managed daily operations and enhanced sales, and earlier positions as Benefits Representative at American Income Life: AO, and Project Manager at Mass Construction and Management Inc., focusing on client relations and project oversight, respectively. Jonathan holds a Bachelor of Business Administration degree from Fitchburg State University.