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Jeffrey Sinkwich began their work experience in 1996 as a Systems Analyst at MassMutual Financial Group. From 2005 to 2006, they served as a Desktop Migration Team Leader at Summit Technologies, Inc. In 2006, they worked as a Quality Assurance Software Developer at Prophesy Transportation Solutions, Inc. From 2007 to 2013, they were an Application Development Senior Specialist at CIGNA. Subsequently, from 2013 to 2014, they served as a QA and Testing Senior Specialist at Cigna - TEKsystems (Consultant). Jeffrey then joined Health New England in 2015 as a Software QA Analyst. Additionally, Jeffrey Sinkwich was also a Traditional Guardsman at Air National Guard from 1985 to 2013.

Jeffrey Sinkwich pursued their education with a focus on business and technology. Jeffrey obtained a Master of Business Administration (M.B.A.) from the University of Hartford between 2012 and 2020. Prior to this, they earned a Bachelor of Science (B.S.) degree in Computer Science from Westfield State University. Jeffrey also holds an Associate of Science (A.S.) degree in Electrical, Electronics, and Communications Engineering from Holyoke Community College. In addition to their formal education, Jeffrey has also obtained a certification as a Six Sigma Yellow Belt.