Generative Artificial Intelligence (GenAI) is rapidly transforming industries and organizations through automation and augmentation. Personalization of human–system interaction is a key area that can be significantly advanced through the effective implementation of GenAI. GenAI, positioned as an intermediary between humans and systems, can transform the human experience from the pre-defined, conventional notions of personalization into a dynamic and integrated hyperpersonalization capability. This article presents the zero-shot-to-head-shot hyperpersonalization (Z2H2) framework, which aims to achieve this through the effective adoption of GenAI techniques. It is a domain-neutral framework of three incremental stages named zero-shot, few-shot, and head-shot that gradually increase the level of hyperpersonalization of the human–system interaction. The framework is further represented in a layered system design and the Z2H2 Data Modality Matrix (ZDMM), which systematically maps data types, AI capabilities, and personalization objectives for each stage. The capabilities of the framework are demonstrated in an educational setting, followed by an empirical evaluation using the Open University Learning Analytics Dataset (OULAD). Although this dataset only contains demographic and aggregated clickstream data, which is a subset of attributes relevant to the entire framework, the gradual development of zero-shot-to-head-shot hyperpersonalization is effectively demonstrated and validated on these student interactions.