The massification of university and its openness to new student population led to the reconfiguration of the higher education system, and to the implementation of institutional policies in order to promote the academic integration of these “newcomers”. Therefore, this research paper aims to analyze the main socio-academic characteristics of students in massive private universities, their difficulties to adapt to the university environment, both academically and dispositionally, and the opportunities that higher education opened up for them. Thus, the perceptions of the management teams regarding the students attending six courses at three private massive universities in Santiago, Chile, regarding their students’ body are analyzed. It is concluded that students in these universities are characterized by common features, but also by differentiating factors (essentially depending on their life trajectories) and that they are influenced by the logic of mercantilism that configure the Chilean education. Consequently, it is concluded that these students’ difficulties concern not only the academic domain but also the dispositional one, requiring the university implementation of active socializing strategies (for both students and families). Despite these barriers, there is unanimous agreement among the interviewees about the benefits of attending university: worldview development, competences, and abilities acquisition, high wage returns and, last but not the least, real opportunities for upward intergenerational social mobility.