The purpose of our research is to understand the benefits Enterprise Resource Planning (ERP) systems render to commercial organizations in Kenya and to understand the challenges that affect the ERP Implementation process. These benefits and challenges have direct impact on the performance of the business; therefore the study seek to understand the complexity of these two factors. Thirty five organizations participated in our research. We established what kind of benefits were realized by various sizes of organization adopting ERP systems, and the differences that exist among challenges and benefits with respect to the size of the organization and age of ERP System. Lastly, our research also identifies how various benefits and challenges are interconnected and interdependent.