Digital transformation significantly reshapes business operations, globalization, management practices, and business processes while posing new challenges in corporate culture, leadership, and resource management. When strategically designed, the efficiency and effectiveness provided by digital technologies increase competitiveness, creating both short-term and long-term benefits and challenges depending on the firm’s market position. This transformation enables companies to deliver value to both the corporate culture and end users in various ways. However, the digital transformation process involves multiple critical decision-making stages crucial to a company’s future and requires compliance with new standards and strategies. This research conducts a systematic literature review to outline and classify the key managerial dilemmas firms face, thereby complicating the digital transformation process for each organization.