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Jonathan Cunningham has an extensive work experience in various roles within the construction and home services industry. Jonathan began their career in 2004 as a Senior Construction Superintendent at America's Home Place, where they oversaw multiple construction projects and managed budgets and schedules. In 2005, they joined Stock Building Supply as the Director of Project Management and Subcontractor Services, where they launched a new division focusing on installation services and managed daily operations, sales team, and field labor. In 2009, they moved to HomeServe USA, starting as a Regional Operations Manager and later becoming the Director and VP of Contractor Operations. In these roles, they managed contractors, negotiated pricing, ensured compliance, and oversaw the deployment of policy jobs across the United States and Canada. Overall, Jonathan has a strong background in operational oversight, contractor management, and customer service within the construction and home services industry.

Jonathan Cunningham attended Brigham Young University from 1996 to 2004, where they received a Bachelor's degree in Construction Management and Business. Jonathan also briefly attended West Virginia University in 1995, but did not complete a degree or field of study at that institution.