Empirical research on coopetition has examined multiple forces that shape the pursuit of coopetition (simultaneous competition and cooperation), but studies have largely concentrated on factors at the industry, organization, or network levels, with limited attention given to the managerial level. Focusing on the top management team (TMT), we integrate theoretical insights from the upper echelons and agency literatures and suggest that the risk-taking propensity of the TMT drives firms to engage in coopetition. We theorize that this positive relationship becomes more pronounced with an increase in long-term compensation but is attenuated by environmental dynamism. Results from the data of publicly traded firms from Taiwan during 2013-2016 provide support for our hypotheses. A supplementary analysis also shows that TMT risk-taking propensity propels firms to pursue simultaneous competition and cooperation rather than aggressive competition. Our theoretical insights and empirical results underscore the role of TMTs in the firm’s pursuit of coopetition and provide a nuanced understanding of how such effect varies across different conditions.