There is a growing number of studies exploring social enterprise in order to increase the understanding of business sustainability and resilience in the social economy. However, little is known about how social enterprises or social entrepreneurs emerging from not-for-profit sectors have faced human resource management (HRM) challenges in practice. In this study, we focus on a hospitality social enterprise founded by social workers in Slovenia as a single case study. Through a series of combined interview and observation methods, we investigate the HRM challenges this social entrepreneur faced when pursuing sustainable social business. We uncovered four strategic and HRM challenges that contribute to the existing body of knowledge in the social enterprise literature. This study paves the way for future studies to focus on HRM in social enterprise.