E-commerce and Internet technologies are fundamentally changing the way companies do business. While much attention is paid to the profitability among the dot-coms and the viability of the new business models, there is much less focus on the impact of the Internet on the work practices of actual workers. As companies are developing new business models, existing work processes have to be adapted to the new environment in which communication is mediated by e-mail and the Internet. This new environment is marked by ubiquitous information access, asynchronous information exchange, and written communication. Depending on the extant information asymmetry and the degree and nature of the contact that workers need with their colleagues, customers, and trading partners, these attributes present both opportunities and challenges. In sales, for instance, a work context characterized by high equivocality, the increasing reliance on lean media like e-mail presents considerable challenges for sales people whose ability to “read” customers is curtailed. In this paper, we report on a two part study that investigates (1) the impact of Internet technologies on the work practices of car sales associates and (2) the antecedents of Internet technology use and sales performance among car sales associates engaged in Internet sales. In the first part of the study, we interviewed car sales associates engaged in Internet sales and, based on their description of the changes in their work lives, we developed a model to predict the use of Internet technology for car sales and sales performance. Since the online sales environment offers sales associates less information about their customers, our central hypothesis is that the initial assumptions with which sales associates enter into a sales encounter playa very significant role in predicting the outcome of the Internet-mediated sales encounter. We test this and other hypotheses using data collected via a national survey of 155 randomly selected sales associates.