The ability to successfully manage organizational transformation has become a competitive necessity for modern organizations. Information technology (IT) can help organizations to change and innovate, yet the presence of IT investment, by itself, is not a good predictor of transformation success. Why do some companies achieve successful transformation while others do not? Through the comparative analysis of five high transforming cases and five low transforming cases, supplemented by large-scale survey data, we identified some characteristics and transformational practices of companies that are more likely to engage in innovation and transformation with IT. The results indicate that successful ‘transformers’ tend to achieve additional value from IT beyond productivity improvement, and this ability depends on the organizations’ innovative culture, leadership, structure, and investment strategy as well as the implementation of transformational and learning practices. The paper suggests how organizations can improve their ability to transform with IT.