The World Health Organization recommends countries adopt policies that encourage the creation of healthier food retail. In Australia, some organisations have created enforceable regulation for healthier food retail in settings under their contractual control. While progressive for public health, little evidence exists on the characteristics of individuals and organisations influencing sustainment of such initiatives. We explored the perspectives of those involved in a sustained (six year) real-world healthy vending initiative in a university setting in Melbourne, Australia. Qualitative interviews were undertaken with seven of the eight individuals involved in the initiative and informed by the Consolidated Framework for Implementation Research and the regulatory concept of social licence. Reflexive thematic analysis was used to generate themes on individual and organisational factors associated with sustainment. Two individual-level themes included participants enjoyment and skills for ‘getting the job done’ and working on innovative projects. Individual self-efficacy and enjoyment from working on innovative projects, combined with interviewees’ perception that their organisation had a role in leading social change, contributed to the initiative’s sustainment. Two organisation-level themes included the University leading innovation and having a responsibility to serve the needs of its community within the constraints of the need for ‘financial viability’ and the provision of ‘consumer choice’. This study brings to the fore evidence on the individual and organisational characteristics that contribute to the sustainment of a healthy food vending initiative from the perspective of those involved in implementation. Exploration of the importance of these characteristics to other food retail settings is required.