Background: People with an intellectual disability prefer more choice with employment options and more community facing roles rather than just traditional supported employment roles. However, data reveal that transition rates from supported to open employment in Australia remain very low and these findings are also found internationally. Method: To examine current organisational and policy barriers preventing transition from supported to open employment, a series of 27 in-depth interviews were conducted with people with an intellectual disability, staff from supported employers, and staff from open employers. Results: There were several key policy and organisational barriers identified. These included inflexible funding models and packages, lack of knowledge and experience of open employers, and insufficient training, pathways, and supports for people with an intellectual to make that transition. Conclusion: The findings highlight some of the broader policy and program reforms that are required, commencing in school and inclusive of all employer groups.