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The automation of activities and the digitalization of services are leading to changes within companies, the need for new skills, and even the emergence of new professions. This article looks at the potential limits of a job-stability policy within a family business. The literature studied includes the theoretical concepts of family social capital, the bivalent attributes of the roles played by the stakeholders in the company, and the resource-based approach. A qualitative study was carried out with twenty-four managers of an international family retailer. The results show that the tradition of lifelong employment is underpinned by family social capital, which permeates managerial style and HR practices, and by strong employee commitment, motivated by an original employee share ownership scheme. Acquiring the right resources to address the challenges of digital transformation requires a rethink of the relationships between the company’s stakeholders, its organization, and the way it operates.