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Jonathan Cleaves has over 20 years of work experience in various technology-related roles. Jonathan started their career at St. Mark's School as a Systems Administrator, where they were responsible for a wide range of technology tasks. Jonathan then worked as a Technology Consultant at Caturano and Company before joining Vitale, Caturano & Company as a Support Engineer. In 2008, they joined Morse Technologies as a Senior Technical Consultant, specializing in leveraging business technology to maximize organizational value. From 2011 to 2021, Jonathan worked at Northfield Information Services, Inc. as a Resident IT, where they played a key role in providing analytical and operating efficiency tools for investment professionals. Jonathan is currently working at Athenium Analytics as a Senior DevOps Lead.

Jonathan Cleaves attended Southern New Hampshire University in 2014 and is currently pursuing a degree in Information Technology. Jonathan has obtained additional certifications, including MCP, although specific details about the institution and the date of obtaining the certification are not provided.