Despite extensive research, many organizations face significant challenges in achieving digital transformation. We conducted a multiple case study to understand how intrapreneurship programs contribute to digital transformation. Our findings reveal that intrapreneurship programs have multi-level effects on digital transformation beyond the development of new ventures. We identify that failed projects foster participants’ competencies, cultural, structural, and technological changes within the organization, and learning capabilities. Our results question the meaning of failure in digital transformation and intrapreneurship research and position intrapreneurship programs as practical means to drive digital transformation.