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Jamie Gilleland has a diverse range of work experience. In 2001, Gilleland worked as a consultant for CompuTrain, LLC. In 2002, they started their own management and IT consulting firm called Jamie Gilleland Consulting, serving government and commercial clients until 2005. From 2004 to 2006, Gilleland held the position of COO at MARS The Real Estate Store, overseeing operations and technology implementation. In 2006, they became the President of MARS Real Estate Corp, leading the franchising arm of the company. In 2007, Gilleland joined Borran Software as Senior Vice President/Operations, responsible for starting the US division and leading organizational change. In 2008, they founded Misyte.com, a company specializing in sales funnels, marketing automation, and CRM design. From 2011 to 2014, Gilleland served as a Director Consultant for BNI, Infusionsoft Sales & Automation Expert. In 2016, they became a colleague at Michael E. Gerber Companies. Lastly, in 2020, Gilleland took on the roles of Elite Coach at Ted McGrath Brands and CEO at GA Commercial Cleaning.

Jamie Gilleland holds a Master's Degree from American Intra-Continental University, which was obtained from 2003 to 2005. Prior to that, Jamie earned a Bachelor's Degree in Information Technology from HOOD and MOUNT ST MARY*S between 1990 and 1994. The educational journey began at Bishop McCort High School, where Jamie completed high school education from 1980 to 1984. Jamie has also obtained certifications in various fields. In 2015, Jamie obtained a certification in Public Speaking from Women's Prosperity Network and became an Infusionsoft Certified Partner from Infusionsoft. Furthermore, Jamie acquired a Certified Partner certification from Digital Marketer, although the specific details of the obtaining month and year are unknown.