The Cape Union Mart Group is a typical apparel retail company faced with the challenge of improving the digital customer experience and accelerating digital transformation in the wake of the Covid-19 pandemic. Due to the pandemic, the demand for e-commerce increased dramatically. However, strict lockdown regulations forbade the delivery of clothing. When the lockdown was lifted, there was an order backlog of four weeks. To add to this challenge, the Group was in the midst of a technology update. They moved their entire information technology (IT) backbone to three clouds and, just a week before the lockdown, launched five new websites for its five different retail chains. The ultimate goal with the technology update was to give the company a competitive advantage by improving the customer experience. However, having to do this at an accelerated pace due to the pandemic posed a number of challenges. The case provides a vivid description of how the crisis unfolded and how Grant De Waal-Dubla, the executive of e-commerce and IT at the Group and his team responded to the challenges, together with the marketing team. Based on the success of e-commerce during the lockdown, the owners of the business then tasked Grant with new, aggressive growth targets. Whilst dealing with the aftermath of the lockdown, Grant’s main challenge is to develop a strategy to reach those targets.