Researchers have acknowledged that women leadership plays an important role in the success of organizations. However, the effects of women leadership on the financial performance of firms are mixed results. This article focuses on women ownership (i.e., critical mass and ownership percentage) as a form of leadership and family ownership as two boundary conditions that help us understand when small and medium enterprises (SMEs) benefit from women leadership. We argue that for women leadership to impact the financial performance of SMEs, women need to have a critical mass to influence outcomes and have power through ownership to influence decisions. We also argue that the effects of these relationships are affected by the context of ownership. These ideas are tested with a sample of 10,696 private SMEs from the country of Colombia. Results indicate that the women leadership enhances SME financial performance through both critical mass and a larger percentage of women ownership. However, family ownership negatively moderates the relationship between percentage of women ownership and SME financial performance. Implications of these results are discussed.