In the rapidly evolving digital marketplace, entrepreneurs increasingly rely on storytelling strategies to build meaningful brand relationships. This study examines the impact of Digital Storytelling Quality on Brand Resonance among entrepreneurs in Tamil Nadu, India. Drawing on brand resonance theory and relational branding perspectives, the study investigates the mediating roles of Brand Authenticity and Customer Brand Engagement, while also assessing the moderating influence of AI-Enabled Marketing Analytics Capability. A structured questionnaire was administered to 250 entrepreneurs across various sectors in Tamil Nadu. Data were analyzed using Partial Least Squares Structural Equation Modeling (PLS-SEM) with SmartPLS 4, including mediation, moderation, and predictive relevance assessment. The model explains 61.2% of the variance in Brand Resonance (R² = 0.612), demonstrating substantial explanatory power. Furthermore, AI-Enabled Marketing Analytics Capability significantly moderates the relationship between storytelling and resonance indicating that entrepreneurs leveraging AI tools achieve stronger branding outcomes. Predictive analysis confirms the model’s strong out-of-sample predictive capability. The findings highlight that storytelling, when perceived as authentic and engagement-driven, significantly enhances brand resonance, particularly when supported by AI-enabled analytics. The study contributes to branding and entrepreneurship literature by integrating digital storytelling, relational mechanisms, and AI capability within a unified predictive framework.