The present research was aimed at exploring the relations between character strengths, well-being, and job performance, as well as between particular strengths clusters (e.g., signature strengths, happiness strengths) and these same outcomes. Drawing on the integrative PERMA model of well-being, our research examined how different character strengths and character strengths clusters predict positive emotions, engagement, positive relationships, meaning and accomplishment at work. Similarly, we also examined how these variables predict supervisory-rated job performance (i.e., proficiency, adaptation to change, and proactivity). So far, our two online samples included n = 103 German and n = 90 Canadian workers from a wide variety of professions, respectively. Preliminary results indicated that teamwork, fairness, social intelligence, perseverance, zest, and leadership were the most important predictors of well-being. Similarly, leadership, perseverance, love of learning, fairness, and perspective are the most important predictors of work performance. Regarding clusters, results reveal that the application of signature strengths, as well as happiness strengths (i.e., curiosity, zest, love, gratitude, and hope) are both associated with well-being and work performance. Our results suggest that some character strengths could be better predictors of well-being and performance at work than others. Limitations and implications of the present research will be discussed.