Fewer women than men hold leadership roles in many fields, including higher education (Johnson, 2016). Despite changes in the demographics of college students (Lumina Foundation, 2015) and the traditional definitions of leadership (Kezar et al., 2006), the number of women declines as rank increases, starting at the role of full professor (Dominici et al., 2009; Johnson, 2016). The traditional path to the pinnacle of academic leadership – the role of the academic president – typically flows from faculty to department chair, dean to provost to president (Moore et al., 1983). Based on this pathway, the academic deanship is frequently viewed as a critical point in the path to academic leadership (Moore et al., 1983; Thrash, 2012; Wolverton & Gonzales, 2000). Yet little research actually examines individuals’ reasons for pursuing the deanship and women lack representation at this critical point in the pipeline (Almanac of Higher Education, 2014; Behr & Schneider, 2015). The purpose of this study is to understand how and why senior women faculty decide to pursue the academic deanship. Using a qualitative, collective case study and awareness of different aspects of identity, this study examines the choice processes for 12 women serving as deans at research-intensive institutions as they reflect on their decision to pursue the academic deanship. This research is framed by Social Cognitive Career Theory (Lent et al., 1984), choice architecture (Thaler & Sunstein, 2008), and decision-making theories (March, 1994). Data collection included a two-step interview process and analysis of participant-generated narratives and visual depictions. Key findings suggest: 1) women choose to pursue the academic deanship in order to make an impact on their college, institution, or discipline; 2) the decision-making processes of women in pursuit of the academic deanship are shaped by their local choice environments, individual ambition, and prevailing assumptions; and 3) previous leadership experience is a critical component in women’s decisions to pursue the role of dean. Implications for research and practice are provided, including a need to systemically challenge the traditional path to academic leadership and to create space for women to lead at their home institution.