More and more organizations are integrating Web 2.0 technologies to enhance their organizational learning abilities. However, relatively little attention has been paid to the use of Web 2.0 technologies in organizational settings. This research attempts to understand what drives a person’s use of Web 2.0 technology in organizational settings. To achieve this objective, we conducted a case study on a specific Web 2.0 technology, podcasting, in a global company to understand what factors influence employees’ perceived usefulness of podcasting. Four factors were identified as having important influence in shaping their usefulness perceptions: information overload, tenure, information privacy, and information relevance. A set of propositions regarding the relationships was also developed.