Skilling unquestionably plays the most practical role in creating innovations which will be financially, socially and economically sustainable in developing countries (DCs). And because we now live in an economic age dependent on knowledge and driven by the rapid and global advances in Information and Communication Technologies (ICT), skilling in ICT is even more important. Key to participating in the knowledge-based economy is the ability to creatively and productively apply whatever ICT is within reach to be e-skilled. While ICT has become an important national strategy in all DCs, e-skilling has not. The emphasis has primarily been on education to produce more ICT and science graduates. The irony in DCs is that more ICT graduates do not necessarily result in greater productive participation in the knowledge-based economy. The result is often unemployed ICT graduates or the increased brain-drain of ICT and science graduates to developed countries. E-skilling is clearly a new strategic problem in DCs. The productivity paradox points to the unique need for DCs to re-think e-skilling so as to create financially, socially and economically sustainable local innovations driven by ICT. While many articles appear on how DCs may participate in the knowledge-based economy, very few offer practical suggestions that are locally relevant in DC contexts. Developing a DC e-skills agenda is clearly of interest. In this chapter, we draw on early efforts being undertaken in South Africa to present progressive perspectives on e-skilling in DCs based on four important provisions; a national budget for e-skills development, an environment that fosters creativity and innovation, a collaborative platform that recognizes the collectivist nature of DCs, and a national support structure that in inclined to e-skills brain-circulation.