Building on the transactional perspective of stress and the complexity theory, we analyzed the effects of personality traits and technostress creators on job burnout by applying the fuzzy-set configurational approach (fsQCA) on a sample of 161 senior managers. Our findings reveal nine substitutable configurations in which different combinations of personality traits may react in different ways to technostress creators and cope differently with job burnout. Five configurations may lead to high job burnout, and four configurations may lead to low and medium job burnout. The multiple configurations provided can help senior managers to understand that there is not a single optimal path leading to high (vs. low/medium) job burnout but rather different paths, depending on different combinations of personality traits. Indeed, our findings can help senior managers to establish “personalized” preventive actions, depending on different combinations of personality traits in order to prevent high levels of stress.