Expanding and strengthening the Aboriginal and Torres Strait Islander health professional workforce is recognised as crucial for improving the health and wellbeing of Aboriginal and Torres Strait Islander communities. The Career Pathways Project is an Aboriginal-led research project funded by the Lowitja Institute. Its purpose is to provide insight and guidance to enhance the capacity of the health system to retain and support the development and careers of Aboriginal and Torres Strait Islander people in the health workforce. The national project has several components. This report presents the methods and findings of the workplace-based case studies conducted in New South Wales (NSW). The aim of the workplace-based case studies was to collect ground-level data from urban, regional, rural and remote regions of NSW. A series of 28 yarning circles and 6 interviews were held with Aboriginal health staff and their managers at both Aboriginal Community Controlled Health Organisations (ACCHOs) and Government health services (including Local Health Districts and a Primary Health Network). This allowed us to explore in depth the factors impacting on careers whilst using a solutions-focus to generate a range of potential strategies for enhancing career pathways. In total, 122 people including 83 staff (57 from ACCHOs and 26 from government organisations) and 39 managers (24 from ACCHOs and 15 from government organisations) from across NSW participated in either a yarning circle or an interview. The Aboriginal health workforce brings to the delivery of services cultural skills, knowledge and values that are uniquely Aboriginal, including vital communication skills and ways of conducting business. These are underpinned by personal experiences of living and working in community, and a lived understanding of what it is to be an Aboriginal person. Aboriginal people mostly want to work in health for reasons to do with community. Having a job, especially stable employment, is another factor. Aboriginal health service managers, whether they work in ACCHOs or government organisations, are interested in an applicant’s strengths and their potential to grow and be a leader. In recruiting they look for staff with a combination of cultural, personal and professional attributes. When it comes to Aboriginal people enjoying a career in the health sector, it seems that there are barriers all along the way. Financial pressures impact at every step. The project also identified important enablers. At the organisational level, career development starts with the ‘right’ governance and management structure and strategies, including a Workforce Development Strategy that includes specific goals and actions to enhance career development and ensure cultural safety. Cultural values must be at the forefront. All staff need to feel valued in the workplace and by the community and be appropriately rewarded. Aboriginal leadership is essential with Aboriginal people in the executive and senior and line management positions. The focus should be on providing opportunities through identified and targeted recruitment, nurturing staff, developing skills and strengthening culture. In this respect, ACCHOs are so much more than an Aboriginal organisation delivering health care; they are a place of opportunity bringing wellbeing to staff and community alike. Strategies to improve Aboriginal career pathways are necessary at multiple levels: within health services and organisations, across the health and education sectors, and in the community. Partnerships will be essential in moving forward