The analysis of ERP system implementation remains both, a source of great managerial interest and academic research. However, one of the challenges of these projects is to convince people of the benefits of having a unified management system, which requires efforts from various business units. Thus, the objective of this research is to understand what the IT and business managers’ perception is about the various benefits and critical success factors that integrated systems can provide to their businesses. In order to identify the benefits, the dimensions of the IT portfolio management (ITPM) were used, likewise, to identify the critical factors, Somers and Nelson’s model was used. To achieve the objective of this study, multiple cases were carried out in three organizations: a hospital complex, a network of pharmacies and a supermarket. In all examined cases, the companies had formal processes of choice and selection of potential suppliers. Regarding to the benefits that ERP systems provide, through the dimensions of ITPM, different benefits were identified within each dimension. It was identify that organizations 2 and 3 consider ERP systems more transactional, while organization 1 considers ERP systems more informational, regardless of the other dimensions. With respect to critical factors, there was also some difference in perceptions, but also some similarities: communication and interdepartmental cooperation, the support of top management, clear objectives/ goals and the supplier support.