The COVID-19 outbreak has had a disruptive impact on the academic context and labor market. Indeed, the pandemic shock in such fields has been related to several changes with implications for young people’s careers and well-being. This two-wave longitudinal study, conducted in Italy, aimed to explore the predictiveness of some individual and organizational factors on students’ perceived employability and well-being. A total of 301 Italian students, aged between 18 and 33 (M = 20.63, SD = 1.99), completed a self-report questionnaire measuring career ambition, university reputation, university commitment, technostress related to technology-enhanced learning, perceived employability, and mental well-being at both time points. A path analysis showed that career ambition, university reputation, and organizational commitment positively predicted employability, which, in addition to such variables, positively affected well-being. In contrast, technostress was identified as a risk factor both for students’ perceptions of finding a job and for their well-being. These findings provide a theoretical contribution to a better understanding of the factors involved in undergraduates’ perceived employability and well-being. Moreover, they suggest the need to improve academic-related variables to enhance individuals’ resources in coping with the pandemic challenges.