Transformation of enterprise software development capability towards modern practice continues to be hampered by false starts, frustration and slow change. Silver bullet methods of every shape and size continue to be peddled within what could be termed a cottage industry. Teams continue to be influenced unduly by community reinforcement, confirmatory bias, myopic thinking or blatant conflicts-of-interest. The net result is that investors in software continue to lose hundreds of billions of dollars annually due to sub-optimal decisions leading to poor business outcomes. It is time to proactively mitigate the risks to software investments and achieve true business agility beyond the buzzwords. The disenfranchisement of these stakeholders has gone on far too long in a business climate that is demanding more for less at an accelerating pace. Better outcomes require empowering teams to make less risky, more informed choices about their ways-of-working. Better outcomes require more intelligent staffing based on a more cost effective supply chain. Better outcomes mean practicing empiricism at scale such that effective and pragmatic governance can be exercised by the fiduciary of software endeavors. This book empowers enterprises to cut through the widespread rhetoric and dogma to achieve efficient and effective practice. To get there, a revolutionary change management and governance strategy is detailed that is both credible and concrete. Rather than stop short by just writing about this strategy, a revolutionary expert system technology called Advisor is described that keeps it real, pragmatic and actionable for the challenges inherent with large scale enterprises.