Nearly two-thirds of all Americans start their working lives in retail jobs. Because of the breadth and depth of retail careers, many with relatively low entry requirements, these jobs can offer many people a pathway to a middle-class life. Numerous retail businesses are exploring strategies to help frontline workers advance through an internal career progression or a platform for external job opportunities. Through interviews with human resources and learning and development professionals in 16 large retail companies, we document how retailers design, implement, and think about approaches to advancement for frontline retail workers. Our study includes insights into the talent challenges businesses face, the strategies they use to help workers advance, the metrics that show whether their strategies are working, and considerations for policymakers in supporting frontline retail worker advancement.