Online labor markets—freelance marketplaces, where digital labor is distributed via a web-based platform—commonly use reputation systems to overcome uncertainties in the hiring process, that can arise from a lack of objective information about employees’ abilities. Research shows, however, that reputation systems tend to create winner-takes-all dynamics, in which differences in candidates’ reputations become disconnected from differences in their objective abilities. In this paper, we use an empirically validated agent-based computational model to investigate the extent to which reputation systems can create segmented hiring patterns that are biased toward freelancers with good reputation. We explore how jobs and earnings become distributed on a stylized platform, under different contextual conditions of information asymmetry. Our results suggest that information asymmetry influences the extent to which reputation systems may lead to inequality between freelancers, but contrary to our expectations, lower levels of information asymmetry can facilitate higher inequality in outcomes.