Responding to a call for research into storytelling within the nonprofit context, the paper contributes to an emerging research conversation about communicating organizational strategy through storytelling. The research analyses one hundred stories across 10 leading organizations to identify how they are being deployed and what that tells us about the underpinning strategy. Through bringing story character, classification, and content together for the first time, the paper presents a holistic perspective on the story construct. It identifies that, when viewed as a whole, the stories told by organizations can be a powerful communication tool for reaching external audiences. However, the research also identifies that their ability to convey strategic purpose through storytelling is moderated by storytelling capability. It finds that organizations with stronger storytelling capability use this craft to differentiate themselves more effectively. It concludes with contributing a new conceptual model for understanding organizational storytelling and a roadmap for practitioners to strengthen storytelling capability.