The aim of this study is to describe adaptive selling of life insurance agents that are in charge of marketing their products directly to the customers . Adaptive selling behavior will be assessed according to their association with individual and organizational factors. Organizational factors in question are job satisfaction and transformational leadership, whereas individual factors in question is psycho- logical capital. Data were collected through self-report questionnaires to 205 life insurance agents of several insurance companies in Jakarta. Further data were processed statistically using ANOVA and regression techniques SPSS to examine the effect of transformational leadership, job satisfaction, and psychological capital on adaptive selling behavior. The results showed that all three independent variables significantly influenced adaptive selling behavior (F = 76.483, p < 0.01), with a score of R2 = 0.533, mean contribution of these three variables jointly by 53.3%. The partial correlation proved that psychological capital showed a significant relationship and tended to be strong connection with adaptive selling behavior, whereas transformational leadership and job satisfaction showed no significant relationship with adaptive selling behavior. From these findings it can be argued that adaptive selling behavior is more influenced by individual factors rather than organizational factors.