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.