The success of your DevOps team depends on collaboration between developers and cloud operations teams, the maturity of development processes, security architecture, guiding software architecture principles, and the ability of the team to automate the delivery of software and infrastructure to customers. These factors, along with infrastructure management and integration challenges, are amplified in a cloud or hybrid environment. UPMC Enterprises is the commercialization arm of UPMC. Our portfolio includes seven health information technology companies and several ongoing initiatives, and our current cloud footprint consists of 12 nonproduction and 8 production environments. In this presentation, we will describe our DevOps implementation plan from inception to cost management. We'll share our operation automation practices and security guidelines for integrating cloud-based services and solutions with on-premises systems. We'll compare deployment automation options and container management approaches. And we'll review our software choices, which included packages provided by vendors such as Amazon, Microsoft, and Dell and open-source software such as GitHub, Artifactory, Jenkins, Docker, and Kubernetes. We will summarize challenges we faced during this initiative, its positive impact on the organization, and our DevOps roadmap for 2017.