The Developing and Teaching Academic Writing (DATAW) Global Online Course (GOC) is a teacher professional development course for writing educators in diverse contexts. The DATAW GOC was designed to employ a flexible, learner-centered pedagogy that combines Backward Design principles, foundational concepts of academic writing, andragogical strategies, and sheltered English instruction standards to create optimal learning activities for a highly heterogeneous group of adult learners with different language skills and teaching experience. It also integrates modeling and scaffolding of teaching strategies, experiential learning tasks, project-based activities, and application of knowledge to GOC participants’ teaching contexts and their students’ needs. In this reflection article, we make connections between our DATAW course design decisions and our observations from course delivery. Teaching the GOC across 8 terms to 850 participants from 103 countries revealed significant variation in teaching contexts, class size, workload, pedagogical practices, educational systems, and English language proficiency. These insights guided our iterative revisions at the end of each term, which allowed for continued tailoring and improvement of materials and tasks in response to the contextual possibilities and inhibitors in participants’ global contexts. By balancing theory and research-based best practices with participants’ real-life needs, the DATAW GOC provided a flexible, responsive platform for educators to improve their teaching practices, ultimately cascading their pedagogical knowledge to positively impact academic writing instruction in a globalized educational landscape.