Through the lens of change management theory, this article focuses on transforming institutional culture at small institutions through grant opportunities. Federal discretionary grants, such as the Department of Education's Title III, Strengthening Institution Program (SIP), provide financial resources for new initiatives to improve student outcomes. Cultural shifts can be challenging at small institutions, where deep traditions and institutional inertia can create barriers to positive change. Initiative fatigue also can emerge, as staff and faculty carry multiple roles with limited resources while balancing increased grant reporting and recordkeeping requirements. Through an iterative assessment process resourced with grant funding, transformational cultural shifts can be leveraged while meeting grant objectives and establishing lasting change that will strengthen the institution and produce stronger student outcomes.