Developing countries have been utilizing information and communication technologies in the management of their business and administrative affairs to improve efficiency and effectiveness; at the national level also, they have been innovative with the establishment of information services sectors. From the initial provision of data entry services some developing countries, as participants in the global software outsourcing movement, have embarked on the development of software for export. Many challenges ranging from insufficient skilled personnel to becoming competitive in a fierce marketplace will be faced. This chapter examines the participation of two small Caribbean countries and describes education and training initiatives and other policy approaches taken by them. The consensus is that, while they will hardly ever make a significant impact on global outsourcing, such small developing countries can achieve substantial economic benefits, stimulate their domestic Information Technology environment and attain an enhanced technological capability.