The great and dynamic possibilities offered by the information technologies (IT) impose new challenges to the organizations. The new capabilities of IT demand that the skills and abilities of the people in charge of the technological management evolve accordingly. In this context we are intrigued by what is the evolution of the Chief Information Officer (CIO) that endows him/her with the capacity to face such challenges? Are there patterns in the evolution of the CIO profile? To answer these questions we integrated the definitions in the literature for the ideal CIO profile with the academic programs of prestigious universities in a conceptual map. Then we interviewed 26 CIOs working in Chile to contrast their profiles with the conceptual map. From the literature review we found several prescriptive features regarding the profile and role of the CIO in modern organizations. Differences were found between the ideal role and the evolutionary status of Chilean CIOs. In spite of the differences, we found patterns for the evolution of the profile that allowed us to propose hypotheses and recommendations for the evolution of Chilean CIOs. Finally, we believe that this paper offers a powerful diagnose of the CIO profile to be used by organizations, IT professionals and universities to set professional and academic paths for success in the IT leading position.