Digital transformation is reshaping the industry, yet companies face significant challenges in adopting new technologies. This study investigates challenges affecting digital transformation of the industry, drawing insights from academic research and consultants’ reports. In this paper, a systematic literature review is conducted to determine the most influential challenges when it comes to implementation of digital transformation. Considering the large number of challenges that organizations face during this process, this paper shortlists the most influential challenges and provides discussion and categorization for each shortlisted challenge. Results highlight the importance of continuous learning and training, cybersecurity, change management, digital strategy and framework, as well as the readiness of the companies to provide large investments for entirely new or improved legacy systems.