The purpose of this paper is to explore the career path preferences of third sector social enterprise managers in the UK. It is becoming evident that small social enterprise are seeking ways to provide managerial career options that are suited to individual and organisational need (Spear and Bidet, 2005; Maher, 2014). A survey and semi-structured interviews were conducted with 40 operational managers working in eight social enterprises. Eight HR managers working in the same eight organisations were interviewed to provide insight into managerial career path management systems in small social enterprises. The findings suggest that operational manager's career path preferences are influenced by the individual's values and career needs and the organisation's ability to provide career path options for managers. This is significant for small social enterprises seeking to retain managers; not through the promise of high salaries but through providing developing career paths that will match manager's career needs.