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Generally in South Africa the commentary about our competitiveness in the retail, financial services, banking and other industries reveals that we are not growing our businesses into the African continent as fast as other countries despite our presence and cultural proximity on the continent. In an attempt to yield an explanation this research explores the IT/IS industry structure in SA looking at both suppliers of services and consumers of IT/IS services along the vectors of productivity, value proposition, design of value proposition and strategic positioning. An IT/IS focus is chosen because this is the main way of enabling business competitiveness in the age were in. 12 in-depth interviews were conducted with Executives leading businesses which provide IT/IS solutions. Through an abductive process a systemic view of these issues is presented and explained in phenomenal terms using Roger Martins ideas around the design of business because of the resonance between the findings here and his ideas on “design thinking”.