"Configure once, deploy anywhere" is one of the most sought-after enterprise operations requirements. Large-scale IT shops want to keep the flexibility of using on-premises and cloud environments simultaneously while maintaining the monolithic custom, complex deployment workflows and operations. This session brings together several hybrid enterprise requirements and compares orchestration and deployment models in depth without a vendor pitch or a bias. This session outlines several key factors to consider from the point of view of a large-scale real IT shop executive. Since each IT shop is unique, this session compares strengths, weaknesses, opportunities, and the risks of each model and then helps participants create new hybrid orchestration and deployment options for the hybrid enterprise environments.