Distance education has provided the foundation for new generations of learning, including courses delivered through various web-based educational technologies, also referred to as online learning. Many post-secondary institutions face the challenge of creating processes and systems to support instructors who are required to design, deliver, and frequently update online courses. Effective online course design prioritizes a student-centered pedagogical approach through active learning and meaning-making using modern technologies. This requires a wide spectrum of experience, technological skills, and pedagogical knowledge that is difficult to achieve. On one hand of the spectrum, are instructors with experience in online course delivery, learning technologies, and knowledge of online learning pedagogies. On the other hand of the spectrum, are instructors with insufficient experience, technological skills and awareness of online pedagogies. This disparity in instructors' experiences, skills and knowledge results at times in a gap in ability. By providing a flexible and interactive model of support to instructors, instructional designers can shorten this gap in theoretical knowledge and practical skills. This paper explores the skill gap that some instructors face in the online learning domain and presents selected approaches to support instructors when transitioning to online courses based on the authors' professional experiences. This paper considers two models of course design support from two unique higher educational institutions in the United States and in Canada, using different learning management systems. The results show that while these models have different contexts, they offer significant insights about common goals, flexible content, and learner-centered course design.