Recent research has focused on the employee’s perspective in experiencing Corporate Social Responsibility (CSR) strategies. The purpose of this work is to empirically investigate the drivers of employees’ long-lasting working relationships when CSR strategies are in place. A sample of 441 employees across 21 small and medium-sized enterprises (SMEs) spanning various industries in Italy is surveyed to collect data on CSR-related experiences. Then, dimensionality reduction techniques and nonlinear models are applied to self-reported data. The empirical analysis reveals the following: (i) at the individual level, intrinsic CSR initiatives are of major importance; (ii) at the organizational level, sudden changes in perceived leadership hit negatively, especially during crises; and (iii) at the intermediate level, promoting happiness at work (HAW) enhances CSR strategies, creating favorable conditions even for dissatisfied workers. Therefore, the investigation enriches the CSR micro-foundation literature by examining the role of multifaceted layers in implementing CSR strategies in SMEs. In turn, this brings important implications for managers dealing with the phenomenon of the “great resignation.”