This chapter explores Amazon’s evolution from a traditional online bookstore to a global leader in e-commerce, logistics, and cloud computing, with a strong emphasis on digital transformation and Environmental, Social, and Governance (ESG) performance. It critically examines the limitations of Amazon’s initial monolithic IT infrastructure, highlighting its inefficiencies, security vulnerabilities, and adverse environmental and social impacts. In response, Amazon undertook a significant transformation by integrating advanced technologies such as artificial intelligence (AI), machine learning, Internet of Things (IoT), blockchain, and Amazon Web Services (AWS). This chapter details how these innovations have enabled Amazon to enhance operational efficiency, automate supply chains, optimize warehouse management, and strengthen governance. Particular attention is given to how AWS facilitates real-time data processing, scalability, and sustainable practices. Furthermore, the use of robotics and smart systems has improved labor conditions and customer satisfaction, while blockchain enhances supply chain transparency and security. This chapter concludes with forward-looking recommendations for further investment in AI, renewable energy, employee well-being, and the development of private blockchain networks. Overall, Amazon’s digital reinvention presents a model of technological innovation aligned with sustainability and corporate responsibility.