To investigate the challenges that high-growth digital startups (“digital gazelles”) face, we conducted an exploratory study of this under-researched class of enterprises at the intersection between information systems and entrepreneurship research (“digital entrepreneurship”) and propose a digital gazelle definition. We base our findings on an interview study with high-ranking representatives of 14 digital gazelles of different company ages and from different countries and industries. By following a grounded theory approach, we identified nine key challenges across the three areas of management, organization structure, and technology/systems. Building on this, we aim to better capture the strong link between the management and the digital technology use of startups in the digital age. Digital gazelles’ leaders can draw on our results to prepare their organizations for further growth.