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Randy Holobaugh has a diverse work experience spanning over two decades. Randy started their career in 2002 with Thomson Reuters as a Computer Operator and eventually took on various managerial roles within the company, including Technical Operations Manager, Change Manager, and Operations Manager for First Line Support. Randy also served as the BS7799 Site Lead, implementing an ISMS framework and achieving BS7799 Certification. In 2011, they led a team of "Smart Hands" engineers as the DataCenter Operations Manager and was responsible for designing and implementing an Inventory Management system for data center equipment.

In 2018, Randy joined Refinitiv as the Director of First Level Support for the Americas, and later in 2021, they moved to the London Stock Exchange Group (LSEG) as the Director of First Level Support for the Americas. Currently, they are working at Duluth Trading Company as the Director of IT Infrastructure & Operations. Overall, Randy has held various managerial positions and has a strong background in IT infrastructure and support.

Randy Holobaugh obtained an M.B.A. in Master of Business Administration from Webster University in 2011. Randy later pursued a program in Leadership for High Performance at Washington University in St. Louis - Olin Business School in 2014. Randy also holds a Bachelor of Science in Business Administration (BSBA) with a focus in Management Information Systems from the University of Missouri-Saint Louis, which was completed in 2008. Additionally, they have a Bachelor of Science in Business Administration (BSBA) with a specialization in Finance from the University of Missouri-Saint Louis, achieved in 2002. There is no information available regarding Randy's education at Missouri University of Science and Technology. Randy also has certifications in ITIL Foundation Level from CSME and ITIL Practitioner from EXIN, although the specific dates of obtaining these certifications are unknown.