This research focuses on the fully online New Zealand Diploma in Legal Executive Studies (DipLEX) at Toi Ohomai Institute of Technology (TOIT) that was first delivered in 2017. The development of an online program was enabled by the review of qualifications that changed the ownership of the qualification from industry bodies to a national framework. The online program has proven to be successful from an institutional perspective. Nevertheless, it has faced some criticism from the very industry bodies that took part in the initial review process that made the decision to remove industry control. Given this criticism and the review of vocational education and training (RoVE) it is timely to reflect on the qualification and its outcomes for graduates and its relationship to industry. The overarching purpose of this qualitative small-scale study is to evaluate the DipLEX to understand the benefits, if any, that have accrued from the use of constructivist approaches, including communities of learning and problem-based learning in the online environment; to explore the applicability of content and teaching techniques to the employment of legal executives; to determine the transferability of the skills and knowledge in the new DipLEX to legal practice, particularly in the short term (e.g., the first six months of employment); and to identify strengths and weaknesses of the DipLEX. To achieve these aims, interviews were held with five graduates and three employer representatives. The findings from these interviews included a range of sub-themes that stemmed from the overarching topics of learning and transition to work and in employment. For the graduates, sub-themes included thoughts on the benefits and challenges of online learning, the benefits of applied learning and the graduates’ views on assessment structures, the role of the diploma in their job search, and initial employment and progression experiences. For the employers’ representatives’ the sub-themes included thoughts on the value of the diploma in law firms, the employers’ lack of understanding about the diploma, their wish list for the learning they would like to see included the diploma program and their views about online learning. Further sub-themes included the employers’ observations on firm-based practices within the profession of legal executives, including their recruitment, initial employment experiences, including the importance of professional development and career progression. Based on these findings discoveries of note were made in relation to (1) online learning, (2) disconnections between education and industry and (3) gender dynamics that provided a basis for recommendations to improve the experiences of students in the online DipLEX program. Despite extensive consultation and reviews, this research demonstrates an enduring gap between education providers and industry. This disconnect needs to be addressed as per the vision of Te Pūkenga. In particular, that the structure of law firms includes gendered practices that hinder recruitment and career progression need to be discussed with the students. Finally, this research demonstrates that online learning can be effective, particularly when strong relationships with teachers are maintained and communities of learning are facilitated.