Technology is transforming not only the practice of healthcare but also professional training and educational models. Developing countries, such as Brazil, are increasingly suffering from a severe shortage of health informatics specialists. Training of professionals in this field is expensive, and there is a limited supply of high-quality teaching resources available. We envision that training in health informatics can be better achieved if cultural and technological barriers are anticipated and the training program is prepared accordingly. We describe our four-year experience of a Brazil/USA training program and discuss lessons learned during its implementation. Eleven onsite courses, one seminar, and two conferences were developed under this unique initiative, which made possible the collaboration among different countries and distinguished leaders in the field of medical informatics.