The purpose of this qualitative study was to gain insight on the nontraditional pathways to a college presidency. Specifically, this inquiry explored the career trajectory of college presidents with experience as a former chief student affairs officer (CSAO). The population of the study was comprised of 12 presidents from a myriad of four-year colleges and universities across the country. Data was collected primarily through semi-structured interviews and supplemented by the curricula vitae of the participants. Through data analysis, three themes emerged: (1) institutional type and fit, (2) academic profile, and (3) fundraising. Furthermore, participants offered advice for current CSAOs or other student affairs administrators who aspire to become a college or university president. Findings from this study indicated the majority of CSAO presidents were employed at small to medium-size institutions of higher education with preference given to small, private colleges and universities. Additionally, like most college and university presidents, CSAO presidents must overcome obstacles as they assume their positions. Faculty skepticism was the most noted obstacle participants encountered. Furthermore, participants advised CSAO presidential aspirants to actively maintain an academic profile to maintain credibility with the faculty. Last, fundraising experience was considered a necessary skill that CSAO presidential aspirants should have to become serious contenders for a presidential position. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]