Globally, HEIs are integrating virtual technologies often with a dual goal of improving efficiencies and enriching learning experiences. Yet, despite these aims, the latter has been less successful. Technology usage for pedagogy is commonly formative as opposed to transformative. While there are approaches to learning with technology that potentially effect meaningful learning experiences, pedagogy is complex. This complexity is further compounded when technology becomes part of the learning experience. For instance, how pedagogy in enacted within virtual environments can differ from face-to-face supported learning. There is a need for a faculty voice when it comes to learning with technology, particularly pedagogues experienced in digital learning. This empirical study, through a series of qualitative interviews, explores HE digital leaders, perspectives, experiences, and understandings of learning with technology. Four themes are identified as result of the data analysis. Firstly, learning with technology is naturalised into HE learning cultures. This renders the nomenclature of blended or digital learning outdated and inappropriate. Secondly, how technology is naturalised into HE cultures differs as it is shaped by distinct disciplinary cultures, and learners who differ in their respective needs. Thirdly, technology is an enabler of meaningful assessment as a form of learning, that is formative and dependent upon collaboration. Lastly, faculty development is critical to effective technology integration. This study contributes to the knowledge about technology-based learning in a number of ways. Findings show that technology and pedagogy need to be considered together and not as separate entities. Most significantly in this relationship between pedagogy and technology, findings foreground the importance of pedagogy and instrumentalise technology as a means to the core purpose, which is learning. Moreover, pedagogy and technology are dynamic as they are shaped by people whose learning requirements differ. The research shows that all HE stakeholders need to recognise the connection between technology and pedagogy and adapt their practices to facilitate learning with technology. Taken together, these findings have important implications for practice and policy.