Digital leadership plays a pivotal role in addressing the needs of the fast-growing and changing scenarios of organizations and countries, mainly affecting and segregating society into different classes. This article aims to identify the challenges and opportunities for Digital leaders who are in touch with the digital practices in marginalized communities and working in various areas of Karachi, Pakistan. The study participants consisted of 15 Heads and coordinators of I.T. institutes. This study is based on a qualitative research approach, and data for the analysis was collected through snowball sampling technique in the marginalized areas of Sindh. A semi-structured questionnaire was designed to inquire about the challenges and opportunities that digital leaders face especially working with marginalized communities. Data collected through semi-structured interviews were analysed through descriptive coding techniques. The findings revealed digital leaders are facing multiple issues related to the implementation and deregulation of digital practices especially in marginalized areas. Whereas, the Pakistani Nation has ample potential to uplift their lifestyles through acquiring skills and utilizing them in the right direction.