A native of Californian, Kiley grew up in Northern California enjoying the history and architecture of the area. He attended California State University in Chico for civil engineering before transferring to Arizona State University to study architecture. He graduated in 2008 with a bachelor's degree from ASU's College of Architecture and Urban Design, with an emphasis in architecture and urban planning history. In 2008, Kiley and his wife Alexandra moved to San Diego and they currently live in a 1920's Craftsman style home.
Kiley is Vice President and Principal Architectural Historian for historic consulting firm Legacy 106, Inc. He served in the design department of several award winning architectural and planning firms in California and Arizona before joining Legacy 106, Inc. in 2010.
He has authored and co-authored numerous published articles and historical nomination reports including city, county, and state historical designations including research and reports on San Diego architects Richard Requa, Irving Gill, and Lloyd Ruocco. Kiley is a current City of San Diego Community Planning Commitee board member and member of the County of San Diego Historical Site Board. He has written hundreds of individual and district historic designation reports. His qualifications exceed the requirements established by the National Parks Service and the Secretary of Interior professional qualifications for architectural historian. Kiley has also lectured on historical architecture focusing on the Spanish Eclectic architecture of Mission Hills and Inspiration Heights for the Mission Hills Heritage organization. He has also authored reports on, studied, and preserved many of San Diego's significant historical resources.