- Gaylon served as President and CEO of Xenith Bankshares and Xenith Bank from 2009 until its 2017 acquisition by Union Bankshares, after which he served as Executive Vice Chairman of Union Bank & Trust during the transition.
- He led Xenith’s 2016 merger with Hampton Roads Bankshares as CEO of the combined company, creating the fifth-largest community bank in Virginia by deposits at the time.
- Earlier, Gaylon spent over 20 years at Signet Banking Corporation, rising to President and COO before its 1997 acquisition by First Union, and later served as President of Timber Resource Management.
- He has chaired Collegiate School and serves on the boards of the Chesapeake Bay Foundation and the Virginia Bankers Association.