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, 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 consulting, creating, and overseeing websites for the school's dean, departments, centers, and programs; training school staff on the Drupal and LiveWhle systems; ensuring the School of Humanities online presence is accurate, up to date and complies with Rice standards, policies, and copyright laws; and that the dissemination of school information is accomplished efficiently, effectively, and accessible to all.

Gaylon has over over 47 years experience working in higher education administration, serving the chancellor and senior vice chancellor of the University of Houston System, the commissioner and assistant commissioner of community colleges and technical institutes at the Texas Higher Education Coordinating Board in Austin, the dean of arts and sciences at McLennan Community College in Waco, and Moody Memorial Library at Baylor University.