Riley began his career as a teacher, teaching history and social studies.[6] He began working for the Library of Michigan after getting his library degree in 1989.[7] He had many roles within the Library of Michigan including being head of special collections, and Michigan eLibrary (MeL) coordinator.[1] He was the editor of the Michigan Genealogist newsletter and 2010 received the Filby Award, a recognition given to the leading family history librarian in the U.S.[7] He played a founding role in the creation of the Michigan Service Hub for the Digital Public Library of America and the Michigan Digital Preservation Network.[8] He worked with Archives of Michigan to create SeekingMichigan, an online resource for genealogical research containing over one million freely available death records.[9]
He served as a state librarian after being appointed in 2014.[2][9] He coordinated the Michigan Notable Books program as well as the Michigan Center for the Book.[6] He worked on projects such as the Post-Pandemic Public Library Project, an initiative to help library directors and their communities reconnect after COVID.[7]
Riley had a career belief in outreach saying "We have plenty of librarians that love books. We now need more librarians that love people."[7] In 2023 he was in the advisory board for the University of Michigan School of Information's Civic Librarian Project, a course encouraging librarians to work with local governments and residents on solutions to civic problems.[7]
