Abstract: The onset of the COVID-19 pandemic has forced all industries to work remotely and move into a digital space. In this light, a case study on ABC Logistics was picked in the landscape of Sri Lanka to investigate their journey in Digital Transformation and the challenges they faced, especially due to the complex nature of logistics and the industry itself being a legacy industry as compared to its peers. The purpose of the study was to understand the digital maturity of the large enterprise and identify the challenges and barriers it faced in creating the enabling environment for the digital transformation to be a success. Impact of employee alignment and the effect it has on the digital goals of the organization was explored in the study. The study was conducted in 2 stages, stage 1 being literature from past research being reviewed and combing it with the findings of stage 2 which was a qualitative approach with thematic analysis of 6 interviews that were conducted with the core digital team at ABC spearheading the digital transformation process in the organization. The enterprise in the case study was found to be in the “Beginner’ quadrant of the digital maturity matrix and the challenges that it faced were different to that of “Digiratis”, “Fashionistas” or �Conservatives� when compared to past research in the logistics industry and other industries undergoing digital transformation. There was a new challenges that was identified in this study namely “Work From Home’ (WFH) which is remote working due to the COVID-19 pandemic that brought in a plethora of challenges in terms of communication challenges, loss in productivity and loss in motivation. It was also identified that digital transformation is not only about technology but a business transformation where leadership and change management are the drivers for success in an organization. The importance of innovation and clear digital goals that is driven top down was highlighted as a factor that cannot be overlooked in an organization striving to standardize and centralize processes to drive growth and improve customer experience as part of the objectives to be achieved through digital transformation of the organization.