This paper is for IT leaders interested in understanding how portfolio analysis creates the visibility and facts needed to navigate a digital transformation program. This paper illustrates CAST's work with GRDF, a large energy provider, and how they leveraged portfolio analysis to jump start their digital transformation. GRDF had previously used testing tools to try and analyze their application portfolio, but the CIO found the company was still lacking an objective benchmark. GRDF worked with CAST to establish a baseline view of risk, complexity and business value for each of their mission critical applications. CAST Highlight was able to quickly analyze more than 100 applications and provide actionable indicators on portfolio risk, cost and complexity.