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What motivates a women's interest group to contribute to a legislative campaign? Do women's organizations use different strategies when targeting descriptive and non-descriptive candidates? On one hand, research on lobbying shows that interest groups use campaign contributions to gain sway with influential legislators. On the other hand, scholars also observe that interest groups will contribute to candidates with whom they already hold strong ties, motivated by an interest in ensuring their allies are elected rather than an interest in ``buying'' influence. Unpacking this strategic tension subnationally, this paper considers how groups lobbying on behalf of women chose between these two campaign finance strategies depending on whether they target descriptive and non-descriptive representatives. Using data on campaign contributions to state legislators between 2000 and 2016, I investigate how electoral competitiveness and past legislative behavior on women's issues predict contributions by women's groups over time. How do these predictive relationships change depending on whether the women's lobby group targets male verses female legislators? Supplementing my data with an interview study of state-level women's lobbyists, I argue that women's groups are more likely to view female candidates as allies, and are thus most likely to contribute when women running for reelection face tight elections. In contrast, contributions to male candidates are instead driven by efforts to reward or incentivize legislative activism for women from less likely allies. In illuminating how relationships between women's lobbyists and legislators change depending on elements of descriptive representation, I speak to the larger question of how pathways towards substantive representation for women- and the strategic choices by groups that can maximize the likelihood of substantive outcomes- are divergent depending on the gender of the legislator.