Over the past five decades, several studies have shown that students' reticence toward choosing a sales career has remained constant. Their lack of awareness and misconceptions regarding a sales job are two reasons behind this negative perception and lack of students' "work readiness." Using a conceptual model on student intention to pursue a sales career, this study has two goals: (a) to understand whether students recognize the changes in the salesperson's role and (b) to investigate whether new understanding of these changes has any impact on students' feelings and perceptions regarding selling as a career choice. After a preliminary qualitative analysis, a survey was carried out in a European country (Italy). Findings suggest that students are partly aware of the salesperson's role, but they have a limited understanding of the evolution that has taken place in that role. In addition, there emerges a new antecedent, "Understanding the salesperson role," that has had a significant impact on students' "Feelings toward selling." This new antecedent stresses the relational aspects of the salesperson's job, highlighting how that aspect has never been considered in previous studies. Different explanations are offered, along with educational and training implications for curricula, program content, and handbooks in HEI (Higher Education Institutes).