The phenomenon of old-age pensioners reentering the workforce is neither new nor unique and has been well-reported in several published literature. However, there are remaining challenges to this group of job seekers whose needs have yet to be well-documented from employer’s perspectives, especially regarding decent work, legal landscape, and organizational culture. Our study seeks to provide a better understanding of the underlying causes of these and to help policymakers introduce social protection policies to create a more welcoming and supportive environment for older workers. The study used a case study from service companies in Thailand that participated in the Thai government’s campaign on promoting older employment. Data was collected from interviews with top managers of the human resources department, and that information was analyzed by thematic analysis. Key findings highlighted that the supportive mechanisms for matching decent work, a room for integrating legal framework, and a culture that values inclusivity and fair treatment of all workers, regardless of age, can enhance the social protection system for older workers. The establishment of a modern database of older workers’ skills, which ensures easy accessibility to both employers and older workers, the establishment of a task force specific for monitoring laws and regulations concerning older employment, and the development of effective measures against workplace discrimination are recommended as effective interventions for social protection.