Gaylon came to Houston in 1990 to join the administrative team of the Institute for Beam Particle Dynamics at the University of Houston. After working for the University of Houston and the University of Houston System's Office of the Chancellor, Gaylon joined the Department of Art and Art History at Rice University in 1995 as its department coordinator. In 2000, Gaylon was promoted to administrator of the Department of Art and Art History and went on to serve dual appointments as the senior administrator for both the Department of Visual and Dramatic Arts and the Department of Art History until July 2016.

In 2016, Gaylon was appointed senior digital information manager for the School of Humanities. In this position, he is responsible for ensuring all school websites are up to date, comply with Rice standards and copyright laws, and that the dissemination of school information and news is accomplished efficiently using online resources.