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Jonathan Shepard has worked for six companies in various roles starting from 2009 to present day. Their most recent position is a Project Engineer II at Sigma Technologies Ltd since June 2023. Before this role, Jonathan was a Senior Designer at Mesa Associates Inc from March 2022 to June 2023. Jonathan worked as a Sr. Electric Distribution Designer at City of Loveland from April 2019 to March 2022 and as an Electric Distribution Designer from March 2018 to April 2019. Jonathan also worked as a Power Engineering Technologist II at Pike Corporation from November 2015 to March 2018 and as a Design Technician at Nueces Electric Cooperative from June 2014 to November 2015. Their earliest role was a GIS Project Coordinator at The Davey Tree Expert Company from April 2009 to June 2014.

Jonathan Shepard has participated in several educational programs throughout their academic careers. In 2004, they attended Valdosta State University until 2006, with no specific degree mentioned. In 2006, Shepard enrolled at Dalton State College but didn't complete any degree program. In 2014, they studied at Pine Technical College and acquired a line design certification.