We are living in times of rapidly evolving technologies, business models, demographics and workplace cultures that bring about a quantum of change that will deeply challenge business leaders. While the majority of businesses have a digital strategy, how will they execute it, if only a fraction of businesses have the depth of skills and IT staff turnover has breached 20%? At the same time, are traditional organizational structures aligned to serve the real customer, to enable the business to BE agile and responsive instead of just DOING agile projects? Rapelang brings her perspective as a digital native and technology entrepreneur on the kind of business leadership today’s challenges demand in order to build and expand digital businesses.