The involvement (or engagement) of employers is critical to the success and effectiveness of active labour market programmes (ALMPs), yet little is known about how street‐level organizations (SLOs) delivering them interact with employers. This article draws on interviews with ‘employer engagement’ staff in SLOs contracted to deliver the UK's principal ALMP, the ‘Work Programme’. Conceptualizing these staff as ‘boundary spanners’ who operated both within SLOs and at the physical boundaries between SLOs and employers, the study found that their day‐to‐day work involved three key types of activities. First, initial business‐to‐business ‘sales’ approaches to employers; second, a complex process of matching of clients to employers’ requirements through intra‐organizational interactions; third, the building and maintenance of trusting inter‐organizational relationships with employers. The strategies and tensions revealed emphasize the under explored, but critical, role of inter‐personal dynamics, both within and at the boundary of SLOs, in the aim of assisting people into employment.