The University of Wollongong (UOW) as an institution has moved towards a “whole of course approach” to curriculum design, progressively rolling out a transformational curriculum model that articulates design principles of transition, synthesis and broadening. This investigation explores how institution-wide curriculum design can be used to promote connectedness and develop employability across the student cohort. Focusing on the five transformational practices of first-year experience, blended learning, ePortfolios, cross-cultural and interdisciplinary learning, and capstones, this chapter explores how these approaches can be used to support students’ connectedness capabilities. The findings suggest that course learning outcomes which are scaffolded around real world learning experiences are key to promoting and evidencing employability. Tasks that are underpinned by social learning theory, help connect students, while intellectually challenging, authentically-focused tasks enable students to develop their communication, teamwork and problem-solving skills. These learning experiences are discussed with consideration towards future course design, and curriculum renewal.