Web-based corporate training is increasingly being used by virtue of the fact that companies need to train their personnel equitably by imparting large amounts of knowledge in an affordable manner. However, it is difficult to establish the precise nature of the key success factors in these endeavors. In other words, companies are not aware of what factors actually influence the final outcome of this kind of initiative. Therefore, this research seeks to investigate some critical success factors associated with a Web-based corporate training program deployed by one of the largest insurance groups in Brazil. As a result, one may conclude that constructivist pedagogical philosophy, authentic task orientation and integral metacognitive support, applied in conjunction, are critical factors for the success of these endeavors. Furthermore, one may also conclude that an intrinsic source of motivation as well as open structural flexibility, applied singly, have some influence on the success of Web-based corporate training.