Digital Transformation is as much about culture change as it is technical innovation, and this talk will address key issues and lessons learned in managing this journey. Managing large amounts of data in rapidly evolving technical environments impacts every aspect of the mission. A central theme of this panel will be connecting relevant digital transformation aspects in various domains, such as finance, business, and logistics data. In this session, we will share examples of challenges and how we overcame them using enterprise data management and leading data platforms such as Army Vantage. Based on our experience doing it for Army clients, we will offer information technology and warfighting considerations for LLMs, RAG-based, Generative, and Agentic AI tools. We will also identify strategies, and policies to more efficiently and effectively optimize data to support strategic decisions. Attendees will: - Learn key definitions and principles with operationalizing data management, digital transformation and AI in an enterprise. - Gain strategic insights through lessons learned from real-world efforts to employ data management, and AI tools in an Army environment. - Understand what Army Vantage is and ways that it has been used to create more data-centric approaches and solutions. Examples and use cases will be used to illuminate the points presented. We will present slides (and a possible demo from Vantage AI Platform) in a style suitable for a general audience from novice to expert and allow time for quality Q&A.