This study examines the impacts of transformational leadership, career adaptability, salesperson creativity and demographic variables on the positive response exhibited by life insurance salespeople to digital transformation. The research method used here was survey research. Self-administered questionnaires were distributed to 318 full-time life insurance salespeople working across different insurance companies in Taiwan. In order to test the four research hypotheses of the study, the data were subjected to multiple regression analysis with the research variables of interest. The analysis confirmed hypothesis 1, revealing that there was a strong positive correlation between transformational leadership and the positive responses from life insurance salespeople toward digital transformation. Hypothesis 2 was also confirmed, which means that career adaptability significantly and positively relates to the rates of positive digital transformation perceptions among the salespeople. In addition, as stated in hypothesis 3, there was a positive relationship between salesperson creativity and positive reactions to the digital transformation. Finally, hypothesis 4 was partially confirmed because age did influence the positive responses while others did not. This study offers novel observations regarding the relationship between transformational leadership and reactions to digital transformation. The findings also confirm and extend earlier research that career adaptability and creativity are two factors that can help individuals deal with technological changes.