Traditional principal training shows gaps in preparing leaders for complex environments. Grounded in continuous improvement theory, this study details two iterative cycles within an accelerated online school leadership program in Tennessee. The program systematically integrated multi-source stakeholder feedback (participants, districts, state leaders) to refine curriculum, enhance responsiveness, and improve readiness. Analyzing mixed-methods exit surveys from consecutive cohorts (N=69; N=74), feedback from Cohort 1 informed targeted adjustments implemented before Cohort 2. Comparative analysis revealed consistent positive trends in perceived graduate readiness across leadership domains, though differences lacked statistical significance (p > .05). Results validate integrating diverse stakeholder feedback via structured loops for enhancing accelerated online programs. Findings support using an iterative, responsive design framework incorporating stakeholder perspectives to build competencies needed for current school demands.