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This comprehensive chapter presents an in-depth look into the concept of IT maturity and its importance in driving an organization’s IT strategy. It illustrates the journey of enhancing IT maturity levels, from initial chaotic practices to an optimized and efficient operation. The chapter provides detailed insights into the characteristics of each of the five stages: Initial, Managed, Defined, Quantitatively Managed, and Optimizing, enriched with real-world examples from startups to giants like Google. It further explores the signs and indicators that help organizations identify their current IT maturity level. If you are seeking to understand your organization’s IT maturity, plan for progression, or optimize your existing processes, this chapter serves as an indispensable guide to navigating your strategic improvement.