A critical quantitative approach, this study connected the relationship between women professional fundraisers and women major gift prospects to assess whether their gender congruence related to an increased likelihood of particular philanthropic behaviors. Quantitative data made up of 27 years of completed gift proposal data reported by the University of Missouri – Columbia were evaluated through the lens of relationship management theory informed by distinctiveness theory. The inquiry assessed three philanthropic behaviors including proposal acceptance rate, repeated giving, and donation amount. The findings indicated: 1) women major gift prospects were more likely to accept funding proposals when cultivated by women professional fundraisers, 2) women major gift donors contributed more average dollars when solicited by women professional fundraisers, and 3) women major gift donors were more likely to make subsequent gifts following their correspondence with women professional fundraisers. These findings suggest that critical fundraising outcomes such as proposal acceptance, donation amounts, and donor retention may all be improved among the growing woman donor population by coordination of their cultivation through women professional fundraisers. The study also found that women fundraisers raised less money overall than their men counterparts, interpreted as a symptom of women’s underrepresentation in charitable organizational leadership, but women fundraisers raise more money than men from women donors.