Financial well-being is foundational for short and long term physical and mental health and social inclusion. Poor financial wellness also negatively impacts employees (poorer employee engagement and productivity), their employers, and the economy more broadly. Attaining and maintaining secure employment is key to financial well-being, yet many in society experience employment instability: job loss, underemployment, precarious employment, poor quality jobs. Two particularly vulnerable groups that have received little attention until recently are older workers and family carers. The proposed project will enhance an existing web-based platform (My MatchWork) designed to help overcome employment barriers so that it serves the employment needs of these two vulnerable populations and extends its reach beyond Alberta. My MatchWork (MW), developed using collaborative, human-centred design, comprises an interactive vocational assessment and guidance tool to help people overcoming employment barriers translate their unique skills into viable employment pathways. A Software-as-a-Service application, machine learning informs the vocational matching component. The tool is coupled with ongoing training and support from MatchWork staff. It delivers accurate assessments for individuals, good matches for employers, and outcome data agencies need to support vocational initiatives. MW is currently beta testing the tool and support package with community partners. To date target at-risk groups include persons with disabilities, single mothers and immigrants, but they aspire to adapt MW to also meet employment needs of older workers and family carers. The project will utilize multiple data sources (nationally representative surveys; qualitative data on older workers’ and carers’ employment experiences; and data collected through the MatchWork platform) to generate knowledge that: contributes to the body of knowledge around employment challenges of older workers and family carers and the potential of the platform to address these challenges; informs product development/enhancement; and demonstrates the impact of the platform on labour market success of the target populations.