Current obesity management strategies are failing to achieve sustainable and favorable long-term results. We propose a more personalized, dynamic, and systemic perspective on the interactions of key determinants and coaching advice on obesity. The aim of this study was to use a systems view on overweight, complexity science, and a transdisciplinary process to develop a five-year personalized integrative obesity-coaching and research program. Managers, medical specialists, clinical psychologists, dieticians, physical- and psychomotor therapists, and lifestyle coaches aligned their perspectives and objectives with experts in systems thinking and systems biology. A systems health model of obesity was used to identify the causal relations of variables with the most influence on obesity. The model helped to align and design a personalized integrative obesity-coaching program and to identify the key variables to monitor the progress and to adjust the personalized program, depending on the goals and needs of the participant. It was decided to use subtyping of participants by a systems biologist, based on traditional Chinese medicine symptoms, as a novel method to personalize the intervention. The collaborative transdisciplinary approach based upon a systems view on obesity was successful in developing a personalized and adaptive five-year obesity-coaching and research program.