The technology described herein provides a keyless entry system and associated method for fleet vehicle management. Secure keyless entry is provided to a user for a vehicle in the fleet vehicle management environment without the user having possession of a vehicle key or a vehicle key fob to gain entry to the vehicle. Additionally, in various embodiments, this technology provides a personalized, programmable access device carried by a user desiring access to a particular locked vehicle in a fleet vehicle management environment, an access control device configured to access electronically an on-board vehicle keyless entry system, and an access chip module electronically attached to the access control device and configured to activate the on-board vehicle keyless entry system and thereby unlock the particular locked vehicle. Furthermore, this technology provides a system with local management, reporting, audit trails, wireless connectivity to each access control device, and self-testing.