This paper presents a novel investigation into how supply-side job seeking interacts with demand-side hiring decisions to reproduce occupational gender segregation. The authors theorize that because female job seekers are less confident of their ability in male-typed jobs than their male counterparts, they will be more responsive to cues from employers. Specifically, job application success will encourage female job seekers to approach similar work in the future; employers’ rejections, on the other hand, will be particularly discouraging, leading women to avoid similar work in the future. Analyses of a longitudinal dataset of three million applications for IT and programming jobs from an online freelancing platform support the theory. Past job-seeking experience, either positive or negative, exerted a stronger effect on how women, compared to men, approached or avoided applying to IT and programming. Because failure is the more prevalent outcome, female freelancers stop applying to male-typed jobs quicker than males. In contrast, analyses in the female-typed writing and translation field did not reveal similar gender patterns. Gender asymmetries in response to employers’ hiring decisions reproduce occupational gender segregation by reducing women’s representation in male-typed but not female-typed fields. Implications for research on gender segregation, careers and hiring are discussed.