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Robert Maxwell has worked at CloudCheckr since March 2019 as a Technical Support Engineer. Prior to this, from August 2017 to February 2019, they were a Supervisor at MAXIMUS. Their earliest work experience was at Sutherland Global Services, where they worked as a Team Manager from November 2010 to August 2016.

Robert Maxwell obtained an Associate's Degree in Computer Information Systems from Monroe Community College, where they attended from 2007 to 2009. Additionally, they received certification as an AWS Certified Cloud Practitioner from Amazon Web Services in July 2020.