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Teddy Caddy has a diverse work experience spanning several industries. Starting in 2004, they worked as a Hardware Technician at Southeast Point of Sale, where they installed and supported Point-of-Sale systems. They also developed web-based reporting for physical POS assets and sales figures. In 2008, they joined High Point University as a Web Developer, and later transitioned to the role of Systems Specialist. In this role, Teddy administered, maintained, and optimized enterprise systems, supported enterprise applications, conducted upgrades, and developed data integration and application enhancements. In 2016, they worked as a Systems Design Analyst at Graphic Visual Solutions. They then joined Thought Leader Select in 2008 as a Ruby on Rails Developer/Admin on a contract basis. Here, they worked until 2017. Currently, Teddy serves as the Director of Cloud Infrastructure at MuniBilling, where they direct the cloud infrastructure and have previously held the position of Director of Infrastructure and Senior Engineer.

Teddy Caddy's education history includes obtaining an MBA from the University of North Carolina at Greensboro, where they studied Business from 2002 to 2006. Prior to that, they pursued a Bachelor's degree from the same university, majoring in Geography with a concentration in Environmental Studies, from 1997 to 2000.