This study aimed to explore that how a principal of higher secondary school perceives his or her role in transforming school into a learning organisation. The purpose of the study was to learn about the strategies that the principal used, opportunities she explored along with challenges she faced, to transform school into learning organisation working under a private sector school system in Karachi, Pakistan. Within the qualitative research design, case study method was employed for an in-depth understanding using semi-structured interviews, focused group discussions, observations and document analysis with the principal, teachers, students, community and governance. The study revealed that role of principal was perceived as transformational in which principal demonstrated various strategies to build learning organisation and addressed the challenges faced during this process. The strategies used by the principal included shared vision, team learning through shared leadership, capacity building, developing an enabling environment, developing a culture of innovation, experimentation, feedback and reflection, and networking with the community. The opportunities utilised by the principal included community support, system’s support, technology and staff’s cooperation. The challenges included parental motivation so as to engage them in school’s policies and procedures, blocking time for teacher for professional development, competitive salary packages for teachers, increased workload for all, political pressures on students’ admission, hiring of good teachers, safety and security problems hindering organisation’s schedules. In order to address these issues timely and effectively, principal utilised systems, teachers, staff and community’s support, which seemed a difficult job otherwise. This study presents several implications for policymakers, professional development institutes and educational systems to empower and support the principals and teachers to create supportive structures and cultures in their schools that enhance the learning of the organisations for their sustainable improvement. Finally, the study presents some recommendations for future research to further explore this area.