An increasingly large segment of the working population is experiencing mental health issues, negatively affecting employees’ quality of life and employers’ bottom line. Consequently, ensuring wellbeing in the workplace has become a high priority for many organizations. In this study, drawing on basic psychological needs theory, we proposed that proactive personality will be related to mental wellbeing through satisfaction of basic psychological needs. In addition, drawing on the trait-by-trait interactions perspective, we expected this mediated relationship to be moderated by conscientiousness. We tested our research model using data collected from 185 employees using a three-wave time-lagged design. As hypothesized, proactive personality related to mental wellbeing indirectly, via psychological need satisfaction, and this indirect relationship was stronger at higher levels of conscientiousness. We discuss theoretical implications and offer practical suggestions based on study results.