Digital transformation has garnered significant interest within the research and business communities, and has become an umbrella concept to address the multiple technological, strategic, operational, and leadership dimensions involved in digitally enabled organizational renewal. Such transformation spans beyond mere automation of existing practices to a radical change of business scope. Despite this increased attention, a shared understanding of exactly what digital transformation encompasses and how a digital transformation initiative can be defined and led is still underdeveloped. This article aims to contribute to this research gap by identifying the multifaceted conceptual and applied dimensions of digital transformation and integrating them into a single, unifying framework. Based on a synthesis of extensive yet fragmented literature and feedback from domain experts, we present a conceptual map (i.e., a canvas) for successful digital transformation initiatives. In addition, we identify the key elements through which one can lead implementation (i.e., roles, competencies, behaviors, and enablers). The article contributes both to academia—by advancing the meaning and constituent factors of digital transformation—and practitioners, with the formulation of a conceptual tool for managers engaged in a systemic design of digital transformation initiatives.