SummaryThe link between work and health outcomes for preconception, pregnant, and postpartum (PPP) working women is complex. Further, innovation and enhanced understanding are required to address the work‐related determinants of maternal obesity. However, workplace health promotion is not typically systems‐based nor attuned to the specific needs and context of individual PPP women. We propose that to improve health outcomes for PPP women, we must understand the pathways between paid work and health for the individual woman by taking a systems‐thinking approach. In this paper, we (a) outline the rationale for why the oversimplification or “dilution” of individual context may occur; (b) present a systems‐informed pathway model (the “Context‐Exposure‐Response” Model) and overview of potential work‐related impacts on health and wellbeing outcomes for PPP women using maternal obesity to provide context examples; (c) further investigate the role of motivational factors from a systems perspective; and (d) briefly examine the implications for policy, practice, and intervention design. It is anticipated that this research may act as a starting point to assist program developers, researchers, and policymakers to adopt a systems‐focused perspective while contributing to the health improvement and obesity prevention of PPP women.