This paper aims to analyze the digital maturity level of a large Brazilian B2B packaging company and the main challenges this company faces on its digital transformation journey. To this end, the authors conducted a case study and took a hybrid (qualitative and quantitative) approach to data analysis. The main findings include the B2B company’s low digital maturity level and its difficulty in transitioning from an operational efficiency-focused culture to a digital one. It can be inferred from the findings that there is a low degree of concordance among the organization’s executives regarding their understanding of digital resources and digital leadership capability. It is also plausible to assume that employees are unfamiliar with digital transformation concepts because the organization is not successfully informing all its staff about the subject. This study points out that digital technologies add another dimension to the challenges faced by traditional businesses, and shows the importance of rethinking traditional corporate culture and organizational boundaries, as well as of exploring new assets, such as data and insights, through a digital lens, thus creating new opportunities to add value to a traditional organization in a digital world.