The use of content management systems (CMS) has radically changed the way that web sites are deployed. The plethora of such systems however, makes the decision-making process a challenging task since there is no available classification for CMS. Our study attempts to identify distinctive characteristics of CMS in order to classify them in performance categories. The analysis of our study incorporates both quantitative and qualitative research methods for the successful triangulation of the identified results. For the needs of the study we explored 570 CMS and identified 51 criteria, which we ranked into six distinctive categories that describe clearly the issue of CMS selection. The results of our study can represent an invaluable asset for the successful outcome of decision-making regarding CMS selection from an organization or individuals, and a competitive advantage for the use of innovation toolkits such as benchmarking.