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Ryan Kennedy began their work experience in 2004 as a Network Administrator at the New England School of Law, where they oversaw server health and stability and ensured quick problem resolution. Ryan then worked as a Technical Design / Implementation and Support Engineer at Worldcom Exchange Inc., where they installed and maintained customer hardware and software, troubleshooted various issues, and provided technical input for quotes and upgrades. In 2013, they joined TDS as a Senior Systems Engineer, responsible for on-site and remote support for clients, including account setup and server migrations. Most recently, in 2021, they became a Remote Support Engineer III at New England Network Solutions.

Ryan Kennedy attended Gibbs Boston from 2002 to 2004, where they obtained an Associates Degree in Computer Science. Ryan also attended Central Catholic High School, but the duration of their enrollment and any degrees or field of study are unavailable.

Ryan Kennedy also acquired a certification in HP StorageWorks MASE from HP in June 2013.