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Phil Cunningham has had an extensive and diverse work experience. Phil first worked as a photojournalist for the Rock Island Argus from September 1980 to September 1983, followed by a role as a photojournalist for the Quad City Times from September 1983 to February 1989. Phil then transitioned to the field of sales and marketing, serving as the VP of Sales and Marketing for VideoData from March 1984 to March 1996. During this time, they managed web, interactive multimedia, and VR applications for various markets and clients including John Deere, Arthur Andersen, and the Field Museum of Natural History. In 1996, Phil became the VP of Marketing for 4C Solutions, a company specializing in warranty and service management software and solutions. Phil worked there until October 2011 and was responsible for optimizing service processes for global companies such as John Deere and General Motors. Following their tenure at 4C Solutions, Phil joined PTC/4CS as the VP of Marketing from February 1996 to November 2011. Finally, they joined Sedona Technologies in November 2011 and held the position of VP of Business Development. Sedona Technologies is a consulting company providing IT and Engineering Services to US companies.

Phil Cunningham attended Western Illinois University from 1975 to 1980. However, there is no information provided regarding their degree or field of study. Additionally, there is mention of Alleman, but no specific details are given about the nature or duration of their education there.