Otago Polytechnic (OP) is currently redesigning and redeveloping its programmes and courses under an institution-wide initiative called Designing for Learner Success (D4LS). This initiative has several phases--design, development, delivery, and evaluation. This article focuses on the processes and considerations in the development phase of D4LS, which adopted a collaborative and agile approach to developing high-quality course content, learning activities, assessments, and resources. A thematic analysis was conducted from a record of challenges and limitations encountered by e-learning designers in the development process. Four themes emerged as the key challenges: workload and timelines, products and process, communication, and capabilities and attitudes. Recommendations are offered for improving the support for e-learning designers and course developers who are undertaking similar institutional initiatives.