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Chris Wolff has a long and varied work experience. Chris began their career in 2003 as the CEO of CW Development Group, Inc. In 2000, they took on the role of Senior Director of Sales at Siebel Systems, and in 2008 they became VP Channel Sales at Cybera. From 2009 to 2014, they worked at EarthLink as Director of Partner Channel Sales, and then at GTT as VP Sales of Global Enterprise. In 2015, they became VP of Cloud Sales at CloudRoute, LLC, and in 2016 they were President at JLB Florida. In 2020, they took on the role of EVP Sales at ShimmerScreen\u00ae, and in 2021 they became VP Sales at both Massive Federal and Massive IT.

Chris Wolff attended OLR from 1971 to 1980, Carroll High School from 1980 to 1984, and the University of Dayton from 1984 to 1988, where they earned a Bachelor of Science (BS) in Banking, Corporate, Finance, and Securities.