This study examined career paths and choices leading to the Senior Student Affairs Office (SSAO) for women at community colleges. Data were comprised of 57 resumes and 11 interviews from SSAOs during the 2008-2009 academic year. Network analysis paired with interviews offer career track and progression profiles with rationale for women aspirants. Analysis of the network data suggested two dichotomies based on career choices: (a) institution paths (changing institutions frequently versus remaining at one institution) and (b) job moves (changing jobs more than four times versus changing jobs less than three times). Interview data are presented in these four profiles addressing choices, experiences, and advice specific to gender issues. Overall results indicate an average of four job changes leads to the SSAO, with most aspirants obtaining a doctorate, pursuing a student affairs career track, and gaining financial management experience. Additional implications for women aspiring to the top student affairs position at the community college level are included. (Contains 2 tables and 2 figures.)