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Jerry Bailey has a work experience spanning from 2013 to the present. Jerry started working at Geek Squad in 2013 as an Advanced Repair Agent, where they communicated with clients, documented their issues, sold relevant services, and created service orders. In 2016, they joined All Traffic Solutions as a Technical Customer Success representative, and later became a Senior Technical Support Specialist. The exact end dates for their roles at All Traffic Solutions are not provided.

Jerry Bailey attended the Huntingdon County Career and Technology Center from 2003 to 2006, where they obtained a Certificate of Completion in Computer Servicing Technology. Jerry then went on to complete their high school education at Juniata Valley High School from 2000 to 2006, receiving a High School degree. Additionally, in May 2006, they obtained a Certificate of Completion in Computer Servicing Technology, although the institution that awarded the certification is unknown.