Nature has inspired inorganic chemists to look beyond the immediate coordination sphere of complexes to tune and optimize reactivity. Two important themes have been the use of pendant proton donors/acceptors as well as incorporating redox-active moieties into ligand scaffolds. However, nature does not limit itself to an “either/or” strategy, and uses both of these features in enzymatic active sites. In this talk, I will describe our laboratory’s efforts at discovering new transition metal complexes wherein the ligand scaffold can mediate both proton and electron transfer. A novel dihydrazonopyrrole ligand displays these features, and when coupled with appropriate transition metal centers enables reversible hydrogen and hydrogen atom transfer. Furthermore, this strategy also facilitates the oxidative activation of strong bonds. Finally, we will show how we can leverage this activity for unique dehydrogenative amination reactivity.