The implementation of information systems at the village level will not be effective without the support of competent human resources and a ready organizational structure. This study aims to examine the implementation of the SIMATA DESA application in Gunung Sembilan Village and Pangkalan Buton Village, Kayong Utara Regency. The method used is descriptive qualitative with a case study method and an interpretive approach that emphasizes the experiences of individual subjects. The results of the study indicate that the implementation of SIMATA DESA is influenced by several main factors: (1) Gunung Sembilan Village has a more systematic organization with a clear implementing unit, while Pangkalan Buton Village only relies on one operator who holds a dual position, causing delays in data input; (2) Operators' digital competence is influenced by age and education, where young operators in Gunung Sembilan are more adaptive than older operators in Pangkalan Buton; (3) The availability of work equipment is adequate, but archive management and internet access are better in Gunung Sembilan; (4) Minimal budget support from the district government limits technical training and mentoring, creating a gap in application mastery; (5) Double workloads cause inconsistent data entry. From an interpretation aspect, there are differences in perception: Gunung Sembilan sees SIMATA DESA as a means of modernization, while Pangkalan Buton sees it as an additional burden due to the lack of formal regulations. The main findings of this study confirm that the success of SIMATA DESA implementation is determined by the digital competence of operators, the support of functional implementing units, and technical mentoring and regular supervision from the district government. Visionary village leadership is key to making this innovation meaningful.