Brazilian companies are increasingly turning to web-based corporate training by virtue of the fact that they need to train their employees within tight budget constraints in a country of continental dimensions. However, most of these companies do not know what the critical success factors in these endeavors are. Therefore, this chapter seeks to investigate some key success factors associated with such digital enterprises. In order to achieve this, the multiple case study method is used, whereby two cases, both conducted within the same Brazilian company, leading to opposite outcomes – a success and a failure – are analyzed in depth. Accordingly, the two aforementioned cases are investigated by using quantitative data analysis based on bi- and multi-variate linear regressions, as well as t-tests. The conclusions were that “Goal Orientation”, “Source of Motivation”, and “Metacognitive Support” were the three critical dimensions in these two web-based corporate training programs under analysis.