The digital divide in general, and between women and men in particular, is a manifestation of exclusion, poverty and inequality, and is likely to continue because of the effects of unemployment, poorly functioning digital skilling programmes and socio-cultural norms in some economies, and further depriving women equal access to digital services. Digital skills provide the poor a catalyst to break out of the cycle of poverty and empower themselves. This paper considers a three-pronged digital skills strategy that will be required for developing countries to break out of the digital divide trap: (1) Monitor the evolving set of digital skills required for employment (2) incorporate a holistic digital skills development strategy into national education programmes, and (3) contextualize skilling programs within prevailing socio-cultural norms that will shape the uptake and impact of digital skilling programs.