The rapid progress of generative artificial intelligence has exposed fundamental limitations in existing evaluation methodologies, particularly for open-ended, creative, and human-facing tasks. Traditional automatic metrics rely on surface-level statistical similarity and often fail to reflect human perceptions of quality, while purely human evaluation, although reliable, is costly, subjective, and difficult to scale. Recent approaches using large language models as evaluators offer improved scalability but frequently lack explicit grounding in human-defined evaluation principles, leading to bias and inconsistency. In this paper, we introduce Quantifying Qualitative Judgment (QQJ), a scalable and human-centric evaluation framework that explicitly bridges the gap between human judgment and automated assessment. QQJ separates the definition of quality from its execution by anchoring evaluation in expert-designed, multi-dimensional rubrics and calibrating large language model evaluators to align with expert reasoning using a small, high-quality annotation set. This design enables consistent, interpretable, and scalable evaluation across diverse generative tasks and modalities. Extensive experiments on text and image generation demonstrate that QQJ achieves substantially stronger alignment with human judgment than traditional automatic metrics and unconstrained LLM-based evaluators. Moreover, QQJ exhibits improved stability across repeated evaluations and superior diagnostic capability in identifying critical failure modes such as hallucination and intent mismatch. These results indicate that structured qualitative judgment can be operationalized at scale without sacrificing interpretability or human alignment, positioning QQJ as a practical foundation for reliable evaluation of modern generative AI systems.