Many factors have been proposed as potential causes for the underrepresentation of women in leadership positions. The present research leverages computational modeling and simulation to examine the impacts of external hiring and developmental opportunities, which may have consequences at different junctures in women’s leadership labyrinth. Two agent-based simulations examined 1) the emergence of gender stratification in gender-balanced organizations and 2) the impact of reducing bias in external hiring and developmental opportunities in gender-stratified organizations. Results revealed that gender differences in external hiring heightened women’s sense of tokenism and their turnover rates and that bias in developmental opportunities increased women’s turnover rates due to a lack of promotions - a “sticky floor” effect. Further, improving women’s leadership representation in gender-stratified organizations may be a rocky road – positive impacts were preceded by elevated turnover for women. Implications for organizational interventions are discussed. All code and datasets are available at https://github.com/grandjam/SamuelsonEtAl_GenderStratModel.