This study aimed to assess the supervisory and technical assistance skills of school administrators in San Juan District to serve as a basis for a professional development program. Specifically, it sought to describe the profile of the school administrators, determine their levels of supervisory and technical assistance skills, and examine the relationships between their skills and personal profiles. The research used a descriptive correlational design and purposive sampling technique to select 30 school heads as respondents. Data were gathered through a validated questionnaire with an average weighted mean of 4.55 and a reliability coefficient of 0.971, ensuring the tool’s consistency and accuracy. The data were analyzed using descriptive statistics and correlation tests. Results showed that the school administrators demonstrated highly competent supervisory and technical assistance skills, with average weighted means of 4.35 and 4.36, respectively. However, no significant relationship was found between the administrators’ profiles (age, sex, civil status, educational attainment, years in service, and relevant training) and their skills. Additionally, a weak positive but not significant correlation existed between supervisory and technical assistance skills. Based on these findings, a professional development program was proposed to enhance the administrators’ skills in classroom observation, providing constructive feedback, resolving conflicts, and integrating technology into teaching. The program includes training workshops tailored to address specific needs and promote continuous learning. It is recommended that the district implement this program to support school administrators in effectively managing and assisting teachers, thereby improving overall school performance.