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Randy Skipper has a diverse work experience spanning over several companies. Randy began their career in 2008 as an Intern in Marketing & Community Relations for the New York Islanders. In 2009, they joined Symantec as a Sales Development Representative and later moved on to become a Client Relations Manager and then a Senior Client Relations Manager until 2013. Afterwards, they worked at Relayware as an Enterprise Account Executive until 2017 when the company was acquired by Zift Solutions. At Zift Solutions, Randy held the role of Director of Sales from 2017 to 2020 and currently serves as the Vice President of Sales.

Randy Skipper obtained a Bachelor's Degree in Business Administration and Marketing from Marist College between the years 2005 and 2009. Prior to that, they attended Harborfields High School from 2001 to 2005, but there is no information available regarding any degree or field of study during that time.