This paper explores the issues and challenges facing employers as they manage degree apprentices in the workplace. It examines the relationship between managers and apprentices undertaking a work-based degree. This research is of particular relevance at this time because of the UK government’s initiative to expand the number of apprenticeships in the workplace to three million new starts by 2020 inevitably bringing a range of pressures to bear on employers (BIS, 2015). The purpose is to share early experiences of employer management of degree apprenticeships, and provide a range of recommendations to develop and improve employer and HEI practice. This paper combines desk research with qualitative data drawn from interviews with a range of cross-sector organisations to investigate the employer’s experience of developing the new Degree Apprenticeships. The data is explored inductively using thematic analysis in order to surface dominant patterns and considers the implications of findings upon current and emerging HEI and employer practice and research. There were a number of key themes which emerged from the data collected. These included the need for effective, employer-led recruitment processes, careful management of expectations, sound HEI retention strategies, employer involvement and board level motivators to ensure organisational benefits are derived from effectively situated workplace learning and a focus upon effective, empowering mentoring and support strategies. As degree apprenticeship standards and programmes are currently at the early stages of implementation, and opportunities, funding and resourcing are rapidly changing in the context of government policy, so too will employer appetite and strategies for supporting degree apprentices, along with apprentice behaviour. This means that additional findings, beyond those highlighted within this paper may emerge in the near future. There are a number of practical implications supporting managerial development and support of degree apprentices in the workplace from this research. These are reflected in the findings, and include the development of flexible and collaborative processes, resources, mentor training and networks. This paper is one of the first published accounts of the employers’ perspective of managing a Degree Apprenticeship within the new policy context in the UK. As a result the work offers a unique insight into the emerging challenges and issues encountered by managers working with degree apprentices in the twenty first century business environment.