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Ryan McGuinness began their work experience as a Workers' Compensation Claim Adjuster at GAB Robins in 1991. Ryan then moved on to PMA Insurance Group in 1998, where they worked as a Claim Adjuster. In the same year, McGuinness joined Rite Aid Corporation as a Senior Director of Risk Management, a role they held until 2016. From 2016 to 2018, they served as the Manager of Risk and Insurance at The Hershey Company. Most recently, since October 2018, McGuinness has been the Vice President of Risk Management at NASCAR.

Ryan McGuinness earned a Master's degree in Counselor Education from Pennsylvania State University from 1988 to 1990. Ryan previously obtained a Bachelor of Arts in Psychology from Muhlenberg College, where they attended from 1984 to 1988. Before their college education, they attended St. John Vianney High School from 1980 to 1984. No degree or field of study information is provided for their high school education.