Old-age retirement benefits are a major concern among the Swiss population but estimating one’s revenue after retirement is challenging due to the Swiss social system’s complexity. In Switzerland, as with many other countries, the risk of poverty for retiree people is high, especially for women who often work part-time. The research presented in this paper proposes a methodology to enable the development of a digital platform to provide Swiss citizens the means to verify that their retirement income will allow them to live decently when retired. The aim of the platform will be to allow insured people to plan for retirement in a simplified manner. The methodology used was both qualitative (focus group) and quantitative (surveys). The main results are recommendations for the scope and functionality for a digital platform to be developed. A main conclusion is the need to limit the platform’s scope to old-age pension only (e.g., excluding survivors’ or disability pensions). Moreover, an outcome regarding the functionalities is the proposition of scenarios such as postponed retirement, additional purchases in pension fund, or changes to individual status. The development of the platform is not included in the article.