This qualitative-phenomenological study aimed to explore and understand the lived experiences of grade head teachers as educational leaders. This also elaborates on how these experiences empower them, as well as how do they cope with the challenges they encounter in the delivery of their duties as educational leaders. There were fourteen (14) participants who took part in this study selected through purposive sampling technique. Of these 14 participants, seven (7) grade head teachers underwent in-depth interview and the remaining seven (7) were grade head teachers underwent focused group discussion. The data gathered were analyzed through thematic analysis. The study was conducted in three (3) selected public secondary schools in Sto. Tomas East district, Division of Davao del Norte. Results revealed six (6) major themes on their experiences: creating best practices as an educational leader, difficulty with the additional workload, managing different roles, maintaining a supportive and conducive environment, providing technical support, and collaborating with stakeholders. To respond to the challenges encountered, participants revealed five (5) coping mechanisms: delegating tasks to colleagues, maintaining collaboration within the team, strategizing on achieving the goals, keeping an open and honest communication and engaging on professional development. Lastly, they have cited five (5) insights that can contribute to better implementation of distance learning modality. These includes: opportunity for personal growth, necessity to adjust to situations and people, provide relevant support to the school, help implement quality and effective education and prioritize self-care. These insights, extracted from participants reflections on their experiences and challenges, provide a holistic perspective on the multifaceted roles of grade head teachers and their key takeaways.