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Chris Penland began their work experience in 1988 as a Communications-Computer Systems Specialist in the United States Air Force. Following their military service, they worked as a Sr Systems Analyst at Unisys Corp for a short period in 1998. Chris then joined Electronic Data Systems as an Infrastructure Analyst and later transitioned to Ciber, where they served as a UNIX Systems Engineer from 1999 to 2001. In 2001, they joined Siemens Business Services as a UNIX Systems Engineer, and in 2002, they moved on to Georgia System Operations, where they currently hold the position of Senior Systems Engineer.

Chris Penland attended the University of Alaska Anchorage and Troy University in Montgomery. However, the specific years of enrollment, degree pursued, and field of study for these educational experiences are not provided.