The consequence of COVID is that previously reluctant companies have begun to realize the value of big data, AI, and machine learning. Although B2B companies were initially hesitant due to their focus on customer relationships, they are reportedly embracing the technology and implementing AI-driven operations. This study explores innovative AI technologies within a global B2B enterprise. Through interviews with top and middle management, and analysis of meeting notes and hard data, the research uncovers psychological and social barriers, as well as two damaging cycles that impede the benefits of AI. The study highlights the importance of change management strategies to overcome challenges, foster technological and organizational learning by addressing siloed thinking and managing competing interests. It also extends technology management and organizational learning theories by relating them to each identified barrier and suggesting potential solutions.