In this chapter, readers are driven through the rather unforgettable journey of digital age, popularised by electronic commerce. With no doubt, the emergence of information technology and its evolvement and advancement over the years have catapulted way business operations are conducted in recent times to newer heights. In addition, in the course of a heightened need for efficacy in organisational and institutional activities and operations and to provide seamless broadened horizons in the delivery of services, leaders and stakeholders have invested in eCommerce in this regard, in attempts to embrace the current wave of doing business. Needlessly, this wave has translated into flexibility in service delivery, an endeavour that calls for strategic planning. Without a delve, deep into the implementation strategies and the targeted customers, it is tempting to conclude naively that all eCommerce solutions render the desired returns on these investments, given the kinds of leadership that prevail at these institutions and organisations. This chapter provides elucidations with respect to electronic commerce and institutions and business organisations systemically. The results from the study also reveal that the obvious is not always as such.