The demands on people in the 21st century pose enormous threats to their psychological well-being (PWB). Because people high in PWB are happier, healthier, and more productive than those who are low, it is morally and economically important for organizations to do what they can to promote the PWB of its members. Based on job demands/resources theory, this study explores how organizations can use knowledge about work design and individual differences to bolster the PWB of its members. We propose that organizations can increase the PWB of members by enhancing job autonomy, thereby increasing organization-based self-esteem (OBSE), which is positively related to PWB. In addition, we propose that resilience might act as a moderator of this indirect relationship, such that high resilience enhances the positive relationship autonomy has with OBSE, and subsequently with PWB. Measures of autonomy, resilience, OBSE, and PWB were obtained online from a sample of 674 organizational managers. SEM results indicated that high job autonomy most benefited (in terms of OBSE) those participants who were low in trait resilience, while providing fewer benefits to high resilient people. Results are discussed in terms of how organizations might enhance member PWB by increasing member OBSE and/or resilience.