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Research has described a typical pathway to the principalship that begins with classroom teaching then passes through the assistant principalship. While there is increasing knowledge of pathways into the principalship and their inherent inequality, what remains lesser known is precisely where along the way, and to what degree, females and educators of color become fewer in proportion. Accordingly, we compare descriptive statistics for five distinct categories of educators that correspond with the common stepping stones along the pathway to the principalship: 1) teachers, 2) principal certification earners, 3) instructional coaches, 4) assistant principals, and 5) principals. By comparing the intersectional demographics (i.e. race and sex) of these distinct groups, we discern junctures through which otherwise qualified candidates are not advancing.