The literature on descriptive and substantive representation focuses on elected representatives, but overlooks the gender of those who play an integral role in policy process (agenda-setting) and outcomes (implementation): The elected’s chief of staff, senior policy advisors, and, in council-manager systems, the city manager. This thesis examines the role policy staff and city manager gender plays in substantive representation. After analyzing staff composition and agenda priorities — gleaned from State of the City addresses — for mayors of the 50 most-populous cities in the United States, I found substantial evidence to support my hypotheses that the chief of staff’s gender, not the elected’s gender, will drive the overall gender of staff as well as the gender characterization of policy agendas. Mayors — regardless of gender — with female chiefs of staff in this dataset have more female staffers and more neutral policy agendas. Mayors — regardless of gender — with male chiefs of staff have more male staffers and mostly masculine policy. In weak mayor systems, city managers’ gender strongly influences mayoral policy agendas, especially in small cities; since most city managers are male, those policy agendas are more masculine, regardless of the mayor’s and chief of staff’s gender. Thus, I find that staff who are involved in the intricacies of policy process and outcome have a stronger influence on policy than the public-facing elected official. These results, supplemented by interviews with mayors and chiefs of staff from across the country, could change the importance scholars place on descriptive representation, and alter scholars’ approach to studying both substantive representation for women and American democracy in general.