This paper explores the development of a flexible, free, online certificate program built on open educational resources to support instructors transitioning to online and non-traditional teaching modes. The program offers multiple pathways to completion, including recognition of prior learning and immersing participants in the online learning environment. We describe the challenges learners had to overcome to engage in the program and how, in doing so, they were able to embrace constructivist and connectivist approaches. These, in turn, afforded them ongoing connections, broke the mold of preconceptions and myths when preparing to engage future online learners, and shaped their practice through exposure to learning theories and evidence-based practices. In this paper, we explore the initial design of the program through the lens of the program facilitators and learners from the first cohort, and share our collective learning and reflections from this process.