This case study explores the opportunities and challenges of the digital transformation journey of French wine and spirits company Pernod Ricard. As part of the transformation, the company launched four key digital programs (KDPs) aimed at using data and artificial intelligence to automate processes and drive data-driven decision-making. The case primarily focused on two of these: D-STAR, a sales recommendation system, and Matrix, a tool that optimized the allocation of advertising spend across brands. The company's future direction with the KDPs depended on addressing resistance, providing effective training and support, aligning with strategic goals, and overcoming logistical and data-related hurdles. The company needed to find a way to expand the KDPs further into new markets while reinforcing adoption where the KDPs had already been launched, and the decisions made would shape the path forward.