After moving with his wife to Winchester, Virginia, Wiley spent several years on the city's Board of Zoning Appeals and Planning Commission.[2][3] In 2014 Wiley ran for the city council and was elected without opposition.[4] From January 2018 onwards, Wiley was president of the city council.[5] Wiley ran for re-election in 2018, defeating Democratic challenger Teri Merrill by a 55% to 44% margin.[6]
In June 2020, incumbent Virginia state delegate Chris Collins resigned from his seat to accept a state judgeship, and Wiley announced that he would run in the ensuing special election.[7] Wiley won the Republican Party nomination for the seat in an August 8 firehouse primary, defeating former Warren County supervisor Richard Traczyk.[8] The Democratic Party nominated attorney Irina Khanin. In the November general election, Wiley defeated Khanin by a 64-36 margin.[9]
Wiley works as a business development manager for a general contracting and construction firm, and as an associate real estate broker.[7][10]