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John Diggins has a diverse work experience history. John started their career as a Computer Science Tutor at Bunker Hill CC in 2018. In 2019, they worked as a Software Engineer Intern at DeepCure and later became a Junior DevOps Engineer at Zaius. In 2020, they joined Area4 Labs Inc. as a Software Engineer and then transitioned to ChaosSearch, where they held various roles, including Software Engineer, Senior Software Engineer, and currently serves as the Technical Lead of Platform Engineering.

John Diggins earned a Bachelor's degree in Computer Science from UMass Boston from 2018 to 2020. Prior to that, they obtained an Associate's Degree in Computer Science Transfer from Bunker Hill CC from 2016 to 2018. In 2009 to 2010, they attended Berklee College of Music for Guitar Performance & Jazz Composition, although no degree was specified.