Voluntary sector and non-profit studies require theoretical frameworks facilitating better understandings of what occurs on the ground. Following Lipsky’s (Street-level bureaucracy: dilemmas of the individual in public service, Russell Sage Foundation, New York, 1980) formulation of street-level bureaucracies, scholars have emphasized workplace hierarchies, reproducing dichotomous ‘top-down’ and ‘bottom-up’ conceptualizations of practice which can obscure the full complexity of practitioners’ workplace relationships. In this paper, we offer a thematic model of (collective) action that centres the ‘division of labour’ across, and relations between, professional niches that are differentiated by their ‘helping’ orientations, workplace tasks, and responsibilities to service users rather than their organizational status or salaries. We mobilize qualitative research undertaken in the penal voluntary sectors of Canada and England to highlight the mutually constitutive efforts of frontline and management work with criminalized service users. Drawing on and extending Alinsky’s ‘river dilemma’, we conceptualize practice in the (penal) voluntary sector as organized according to the differing choices practitioners make about whom to ‘help’ and how to intervene, which have consequences for social policy, service delivery, and advocacy work.