The rapid digital transformation of higher education institutions (HEIS) in the National Capital Region (NCR), Philippines, has redefined the way academic and administrative work is conducted. While technology has enhanced accessibility and operational efficiency, it has also given risc to technostress-psychological strain caused by the constant use of digital tools and the demands of remote work. This study investigated the relationship among technostress, remote work, and organizational performance in selected HEIs. Employing a descriptive-correlational research design, data were gathered from administrators, faculty, and non-teaching personnel through structured surveys. Results indicated that technostress is moderately experienced, particularly by administrators due to their broader responsibilities. However, it does not significantly correlate with remote work practices or organizational performance. A slight negative correlation was observed between remote work and organizational performance, suggesting potential issues in collaboration, alignment, and communication in a virtual work environment. Despite these challenges, respondents generally viewed remote work and institutional performance favorably, especially in areas such as quality of service, goal achievement, and stakeholder satisfaction. The study also identified hindering factors like system inefficiencies and poor communication, and facilitating factors such as IT support, training, and leadership engagement. Based on these insights, a Strategic Development Plan was proposed to enhance digital competency, promote mental wellness, improve communication systems, and support flexible work arrangements. The proposed plan was evaluated as highly suitable, acceptable, and feasible by all respondent groups. These findings underscore the importance of institutional strategies that align technological advancement with employee well-being and organizational effectiveness in a digitally driven academic environment.