While enterprises invest heavily in optimization models, critical decisions remain manual and biased. This session details the real-world journey of transforming traditional Operations Research (OR) systems into true decision intelligence platforms. By integrating optimization with Generative and Agentic AI, we move beyond static dashboards to interactive, explainable, and context-aware decision-making. Drawing from large-scale air network planning, we show how GenAI acts as a translation layer, enabling planners to understand and trust complex model outcomes. We then explore how Agentic AI takes the next step, proactively analyzing scenarios and recommending actions to achieve strategic goals. We’ll cover the foundational shifts in data architecture and ontology required for this convergence and the challenges of scaling these systems. This is an execution-led perspective on how OR and AI together are creating a more intelligent and autonomous enterprise decision loop.