The transportation and warehousing sector employs nearly 5 million individuals, many of whom are transport operators. Transport operators have experienced changes in work organization in recent decades; however, little is known about the impacts of these changes and how these impacts differ between operator types. Therefore, using two directly comparable transport operator datasets – one of all transport operator types by the National Sleep Foundation, and another of exclusively long-haul truck drivers called the Trucker Sleep Disorders Survey (TSLDS) – we sought for the first time to evaluate disparities between transport operators’ work organization; sleep characteristics; sleep problems and sleep disorders; and safety outcomes. We also explored associations between work organization and sleep characteristics, problems, and disorders with safety outcomes. Many significant differences were found across transport operator sectors. In particular, the TSLDS long-haul truck drivers largely fared worse when compared to other transport operators across a number of characteristics, including shift length, shift work, sleep latency, and the number of safety outcomes due to sleepiness. These cross-sectoral differences suggest the need for tailored interventions to address the unique configurations of demographic, work organization, sleep, and safety characteristics found in different transport operator sectors. However, across all transport operator sectors, latent sleep disorders appeared ubiquitous; thus, universal efforts to screen, diagnose, and treat sleep disorders should be a public health imperative. Differences were found transport operator in patterns of significant associations between work organization and sleep with safety outcomes, further suggesting the need for tailored interventions. However, sleep quality, sleep sufficiency, and whether one's workday schedule allowed adequate sleep were the most strongly associated with safety, suggesting that addressing these issues could benefit many transport operators. Further research, including a national study of transport operators, would help guide future interventions to enhance safety