The vocational orientation of the youngsters who are about to enter, study, or have recently graduated at higher education (HE) institutions, and linking HE with labor market are two research areas which have not been investigated extensively in Balkan countries. Job (or occupational) profiles, among other tools used in vocational orientation, provide standardized and digitized descriptions of different professions. This article focuses on the analysis and the design of a web-based decision support system (DSS) to assist its users in getting thoroughly informed about HE studies in Greece, and eventually in choosing their vocational prospects. Apart from reviewing the related previous research work and relevant web-based systems, we present the main elements of the system?s analysis and its design, the extensions that could lead to even more powerful systems, and conclusions about the advantages, limitations and practical application of the DSS.