We investigate how venture leaders can effectively manage stalemates that arise after hiring professional executives. Using a multi-case inductive method, we analyze 21 actual top management team (TMT) stalemates—communication breakdowns between task-dependent parties—within four Hong Kong fintech ventures that raised venture capital. Our study contributes to the venture professionalization literature in several ways. We introduce negative intra-TMT dynamics into the literature by identifying stalemates that emerge during the professionalization process and classifying these stalemates as horizontal or vertical. More importantly, we develop a contingency framework that consists of four actions taken by the venture leaders to manage these stalemates. Our framework reveals that effective leaders use private mediation in horizontal stalemates and structural crafting in vertical stalemates, but not vice versa. In contrast, open discussion and decision enforcement, two actions suggested in prior conflict management literature, were found ineffective for all types of stalemates in our data. Beyond venture professionalization, we offer a fresh lens on conflict management as brokering by highlighting the space and hierarchy in the brokering process. We conclude by suggesting boundary conditions for our theoretical framework.