Critical success factors for technological initiatives are extensively discussed in literature. In order to compare them in ERP and CRM projects, we will use a three-dimension approach of CFSs, which groups them around technology, process, and people. Based on our experience and previous work, we will hold the most relevant factors, and then discuss their incidence in CRM versus ERP initiatives. We will design the ERP/CRM CSFs representation, supported by the practical research, where we have investigated the CRM initiatives in Romanian companies. Through our study, the paper (a) provides an outline of literature pertaining to the critical success factors; (b) yields insights into differentiating factors in the ERP and CRM implementations, and (c) offers evidence of how Romanian companies deal with technological initiatives in their striving for success.