Although the results of the HTE campaign are seemingly outstanding by academic and medicinal chemistry standards, significant improvements, especially in regioselectivity (>98:2), were desired for more efficient manufacturing. The lack of intuitive trends relating ligand structure to reaction performance made it difficult to suggest improved ligands. For example, when Segphos L5 was replaced with L7, increased regioselectivity is observed but with a concomitant reduction in enantioselectivity (Fig ). Similarly, in the Rh-catalyzed hydroformylation, replacing L6 with L11 improved the reaction conversion but with an associated erosion of regioselectivity. This highlights the complexity of the multi-objective optimization problem and why a data-driven workflow was pursued. Additionally, we recognized the opportunity to evaluate how the workflow manages the contrasting nature of the two catalytic steps. Not only do the reactions use different transition metals (i.e., Pd vs Rh), but the coordination geometries of putative reaction intermediates are also distinct. While the Heck reaction primarily involves square-planar Pd species, the hydroformylation reaction is thought to proceed through trigonal bipyramidal Rh intermediates.