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Jonathan Bailey has a work history that includes various roles in the construction industry. Jonathan started in 2013 as a Project Superintendent at Homes By Dickerson, where they worked until 2017. In 2017, they became a Project Manager at the same company before eventually being promoted to Division President for the Charleston division in 2018. Prior to working at Homes By Dickerson, Jonathan worked as an Estimator at Kenna Custom Painting, Inc. from 2010 to 2012.

Jonathan Bailey attended East Carolina University from 2007 to 2009, where they obtained a Bachelor of Science degree in Construction Management.