This study proposes measurement systems for assessing the success of implementation, challenges of implementation and success of utilization of enterprise systems. The proposed measurement systems are used empirically to assess the level of success and challenges of a sample of 2500 Canadian and American large corporations in the implementation of enterprise systems. Based on the findings of the study, a comparative analysis of the Canadian and American corporation is presented. The findings show that US firms are more successful in following their ES implementation master plan, in implementation of ES, and face fewer challenges. However, we did not find a significant difference between Canadian and US firms in success of utilization of ES.