This study examines the role of text-based direct messaging systems in online labor markets, which provide a communication channel between workers and employers, adding a personal touch to the exchange of online labor. We propose the effect of workers’ use of the direct messaging system on employers’ hiring decisions and conceptualize the information role of direct messaging. To empirically evaluate the information role of the direct messaging system, we leverage data on the direct messaging activities between workers and employers across more than 470,000 job applications on a leading online labor market. We report evidence that direct messaging with a prospective employer increases a worker’s probability of being hired by 8.9%. However, the degree to which workers benefit from direct messaging is heterogeneous, and the effect amplifies for workers approaching employers from a position of disadvantage (lacking tenure or fit with the job) and attenuates as more workers attempt to message the same prospective employer. The effects also depend on message content. In particular, we find that the benefits of direct messaging for workers depend a great deal on the politeness of the workers, and this “politeness effect” depends on several contextual factors. The beneficial effects are amplified for lower-status workers (i.e., workers lacking tenure and job fit) and workers who share a common language with the employer. At the same time, the beneficial effects weaken in the presence of typographical errors. These findings provide important insights into when and what to message to achieve favorable hiring outcomes in online employment settings.