This paper analyses local employment strategies for shrinking and ageing labour markets through the case study of two local initiatives in Marijampolé, Lithuania. Drawing from desk research, quantitative analysis and primary interviews, the paper determines the effectiveness of Marijampolé’s Third Age University and the Petras Kriaučiūnas Public Library in re-training older workers to improve professionalism, entrepreneurialism and skills development, particularly in information and communication technologies. The analysis also draws synergies between national, regional and local strategies to reskill the Lithuanian labour market to outline appropriate strategy and implementation recommendations for policy makers.