US retail markets are characterized by consolidation, globalization, and the spread of big-box discounters. What do these trends mean for job quality and workers? For compensation, skill content of jobs, and opportunities for promotion? What role do institutions—regulatory, or representative—play in shaping company strategies, and outcomes for jobs as well as workers? Retail generates a large and growing volume of entry-level jobs and is a rare industry with few educational requirements at entry. It is a highly relevant area of the labor market to examine to understand opportunities for low skill and mid level skill workers. Findings come from case studies in eight food and eight consumer electronics companies; a total of 18 cases because two companies had both lines of products. Food retail is the largest subsector and employs a majority of women while consumer electronics employs a majority of men. Data include 195 interviews with: headquarter managers for human resources and operations; regional managers; store managers; union representatives, and frontline workers—part-time and full-time. These are complemented with company HR numbers and sectoral statistics. Retail jobs are affected by significant change as companies struggle to survive and grow in an increasingly saturated market. Strategies include seeking to increase service, and product quality or variety (altering the mix of products and services), on one hand, while also cutting costs on the other hand. However, increased demands on workers combined with low compensation undermine service improvements. The paper explores the match between competitive strategy and labor strategy in the cases. It examines market and institutional conditions in which this two-pronged strategy succeeds and others where it encounters major challenges.