Similar to most West-European countries, the retailsector in Belgium forms a sizable segment of the labor market, characterized by challenges for labor quality and trade union work. This sector, with a relatively large share of precarious employment and workers with a weak negotiating position, is at the same time the setting for intense ongoing discussions on the impact of ‘digitalization’. For example, the impact on labor (quality) of the growth of e-commerce, the emergence of hybrid players such as Amazon, self-scan checkouts, robotization of warehousing, etc. In these debates, management- and policy discourses stress the possibilities for upskilling and more “high route” retail-jobs due to technology-uptake and e.g. a shift to “shopping experiences”. These optimistic expectations stand however in stark contrast with current and short-term expected employment outcomes of hard discounter-competition, such as an increasing share of precarious employment forms, work intensification, monitoring through automatically collected metrics, etc. Diverging expectations like these tie in with the more critical literature on historical evolutions in retail work, such as deskilling through the introduction of technological innovations (e.g. Price, 2011). Drawing on a literature review, expert interviews, and mainly focus groups with 80 shop stewards in food and non-food retail, we explore these underlying tensions in the context of digitalization-trends. We focus on reoccurring, bottom-up topics of work intensification, control over job reconfiguration, precarization, and de/upskilling processes. As the research is part of a broader research agenda for trade union strategy in the Belgian retail sector, we link these topics to a discussion of shop steward strategies and trade union power resources. Given the enduring relevance of institutional characteristics in explaining labor outcomes at the level of retail organizations (Carré and Tilly, 2017), we contextualize these tensions, topics, and shop steward strategies within the Belgian institutional framework. We thus aim to contribute to the research literature on two points. Through the analysis of the qualitative empirical material, we deepen the understanding of organizational level tensions, strategies, and discourses on retail work. Secondly, we complement comparative research on retail work, in which Belgium has been relatively absent. Currently faced with mounting pressure on the still relatively robust union density rates, sectoral collective bargaining, and historical corporatist compromises, the retail sector in Belgium provides an interesting case for trade union responses to contemporary challenges in retail work.