Within organizations, happiness of employees is of key importance, and researchers have theorized that work happiness is comprised of positive well-being and job satisfaction (Sgroi, 2015; Wright & Cropanzano, 2000). However, women experience the workplace differently than their male counterparts (Clark, 1997). In the present study, we examine how female leaders and non-leaders (compared to male leaders and non-leaders), experience well-being and job satisfaction, as well as how work enjoyment predicts well-being and job satisfaction. Participants (286 women and 255 men) completed a demographic measure, the Subjective Vitality Scale (Ryan & Frederick, 1997), the Job Satisfaction Survey (Macdonald & McIntyre, 1997) and the ENJOY (Davidson, 2018). Results showed that being in a leadership position, not gender, determined well-being and job satisfaction with those in leadership positions experiencing higher levels of both variables. For women, number of individuals supervised and leadership experience did not predict well-being or job satisfaction. Last, for women, the work enjoyment variables of pleasure, relatedness and competence predicted well-being and job satisfaction. Results were similar for male participants. Unlike earlier research, the results of the present study found more similarities than differences between women and men. Differences in well-being and satisfaction were more influenced by whether one was in a managerial role than by gender. Future research would do well to focus on exploration and understanding of how female leaders versus non-leaders experience the workplace.