The flipped learning model has emerged as an innovative approach to fostering active learning and engagement. However, its implementation is often hindered by challenges such as addressing learners’ gaps in prior preparation, feedback exchange, and team regulation. This study explores the integration of Generative Artificial Intelligence (GenAI), specifically ChatGPT, a GPT-4-based conversational agent, and the FLeD tool—a learning design platform utilizing predefined pedagogical patterns—to support educators in designing flipped classrooms while addressing these gaps. Through a hands-on workshop with 18 educators and researchers in higher education, participants engaged in the design of learning scenarios specifically for flipped classrooms, utilizing GenAI for brainstorming, the FLeD tool’s pedagogical patterns, and a combined approach. A qualitative and quantitative analysis of participants’ experiences revealed that the integrated use of GenAI and pedagogical patterns offers the most valuable support—combining structure with creative adaptability. While educators appreciated the flexibility and contextual relevance of the combined approach, they emphasized the need for better alignment with real-world curricula. The findings highlight practical implications for enhancing Human-AI collaboration and supporting teacher-led innovation in learning design. Suggestions for enhancing the FLeD tool with GenAI include improved interactivity, structured prompts, and tailored responses to support diverse educational needs.