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The challenge of predicting retail sales on a product-by-product basis throughout a network of retail stores has been researched intensively by applied econometricians and statisticians for decades. The principal tools of analysis have been linear regression with Bayesian inspired adjustments to stabilize demand curve estimates. The scale of such analytics can be challenging as retailers often work with more than 100,000 products (SKUs) and typically operate networks of hundreds of brick and mortar stores. Department and grocery stores are excellent examples but fast food restaurants also require such detailed predictive modeling systems. Depending on the objectives of the company, predictions may be required for blocks of time spanning a week or more, or, as in the case of fast food operators, predictions are required for each 15-minute time interval of the operating day. The authors have modernized industry standard approaches to such predictive modeling by leveraging advanced data mining techniques. These techniques are more adept in detecting nonlinear response and accommodating interactions and automatically sifting through hundreds if not thousands of potential factors influencing sales outcomes. Results show that conventional statistical models miss a substantial fraction of the explainable variance while the new methods dominate in terms of performance and speed of model development. Accurate prediction is required for reliable planning and logistics, and optimization. Optimization with respect to pricing, promotion and assortment can be asked for relative to a variety of objectives (e.g. revenue, profits) and short term and long-term optimization may result in different decisions being taken. A unique challenge for retailers is the large number of constraints to which complex retail organizations are subject. Contracts and special understandings with valued suppliers severely constrain a retailer's flexibility. For example, certain products may not be promotable (or discounted) in isolation, and others (say from competitors) may not be promoted jointly, and the costs of goods sold may well depend on the quantities contracted. We discuss how we have resolved such challenges via a cycle of prediction and simulation to develop a flexible high-speed system for handling arbitrary constraints, arbitrary objectives, and achieve new levels of predictive accuracy and reliability.