Boundary layer clouds can organize into mesoscale (O(100 km)) patterns of clustered cloud structures. Mesoscale organization influences low cloud radiative properties globally, through modulating both cloud amount and opacity, and contributes to the tropical hydrologic cycle, through its role in convective energy discharge-recharge cycles. Trade-wind cumuli occur with varying degrees of organization and are a large source of uncertainty in global climate models. The linkage between trade cumuli development and dynamics is especially difficult to capture in climate models, impacting low cloud feedback estimates. In this study, we utilize in situ observations of the wintertime trades, including from a ship-based Doppler wind-lidar, to investigate the relationship between mesoscale organization and cumuli updraft dynamics. Unorganized periods when small cumuli dominate are contrasted with organized periods featuring a mixture of large (clustered) and small cumuli structures. We observe that cumuli structures are dynamically more efficient when more organized: they have stronger cloud base updrafts — more efficiently moving moisture into clouds — than less organized clouds of equivalent cloud base core sizes. Differences in vertical velocity also extend through the depth of the sub-cloud layer. While unsuccessful, clear-sky thermals have similar size distributions in both periods, more organized clouds tend to develop from wider thermal plumes. These are likely signatures of mesoscale circulations feeding back on organized clouds, reinforcing dynamic efficiency and supporting their continued development. Differences in cloud development dynamics across mesoscale organizational states has important implications for understanding and simulating cloud behavior under future climates and warrants further investigation.