The Greater Cleveland Regional Transit Authority (GCRTA), established in 1974, is a multi-modal transit agency that serves Cleveland and surrounding suburbs in Cuyahoga County, Ohio. GCRTA Radio/ITS system planning started in 1998 to replace an existing radio system and deploy new ITS technologies to increase the overall quality of GCRTA’s service delivery while minimizing operating cost and increasing safety. The technologies were expected to assist GCRTA in real-time service monitoring and archived data analyses for resource and capacity management, service adjustments, and efficiency in data reporting. The deployment process took 10 years, and the system was finally accepted in October 2012. This study was an assessment of the deployment process and documents the impact of technologies on GCRTA business functions.