The aim of the study was to examine the role of migrants in cross-border learning in occupational contexts. The research data included 78 semi-structured and 20 life-course interviews with people who had migrated from Estonia to Finland or who were transmigrating between these countries. The interview data were analysed qualitatively through a combination of data-based and theory-guided content analysis. The results showed how the migrants had engaged in transnational brokering and boundary encounters between work communities across national borders. Transnational brokering had involved introducing new work techniques, clarifying organizational cultures, conveying best practices and explaining local work requirements and communication styles. These transnational brokers had supported the processes of perspective making and perspective taking by explaining local work practices and, more broadly, mind-sets to non-migrants both in the host society and in their country of origin. Theoretical concepts from situated learning theory and transnational migration studies were applied in the analysis. The study provides a new perspective through which to examine international and multicultural work environments and the transformation processes related to the increasing cross-border mobility of labour.