An investigation of several potential explanatory factors underlying the discrepant gender distributions within STEM (science, technology, engineering, and math) field positions across different higher education institution types was undertaken. Data collection consisted of a main online survey of a nationally representative sample of STEM faculty members from a variety of institution types (N = 4, 195) and a follow-up survey of a subset of main survey respondents (N = 712). Regression analyses were conducted to assess predictors of initial job preference, work hours, and WFC (work-family conflict). Family friendliness ratings of research jobs, work centrality, and rated importance of the family friendliness of various jobs during one’s initial job search predicted initial job preferences and displayed significant gender differences, so these variables are supported as explanatory factors underlying the discrepant gender distributions across institution types. In predicting work hours, the presence of dependent children was associated with significantly reduced work hours among women but not among men. Workload emerged as the only consistent significant predictor of WFC. Comparisons of respondents employed at research-focused and teaching-focused institutions revealed nonsignificant or smaller than expected differences in workload, WFC, and work centrality. These findings run counter to reported faculty beliefs that jobs at teaching-focused institutions are more family friendly than those at research-focused institutions. Women reported adjusting their work goals and habits in order to accommodate their family goals, and vice versa, more frequently than did men. Women frequently reported heightened commitments to their families, relative to those reported by men, although in some cases the predicted gender differences were not observed or were of smaller magnitude than was expected. Analyses were conducted separately for two cohort groups created by splitting the sample at year in which PhD was earned. These two cohort groups differ in meaningful ways with respect to the relationships among the variables under investigation, such that many observed gender differences were isolated to, and/or were stronger within, the group of earlier PhD earners as compared to the group of later PhD earners. These results highlight how and why male and female faculty members differ in their early career planning decisions and their behaviors and adjustments within the context of their STEM higher education career paths.