Redox flow batteries (RFBs) are promising candidates for grid storage, but current systems have not met the stringent cost and/or safety requirements needed for widespread implementation. Replacing vanadium with organic compounds may lower materials cost, and utilizing non-aqueous (aprotic) electrolyte solvents, in place of water, could enable a 2- to 3-fold increase in operating voltage. Both features make non-aqueous RFBs candidates for large-scale stationary storage. A limited number of organic compounds have been reported as stable electron donors and acceptors, with even fewer materials being studied as small molecule two-electron donors and/or two-electron acceptors. Our recent efforts have focused on the development of highly soluble electron donors and acceptors with stable oxidized and reduced states. This presentation will focus on design strategies utilized to increase molecular stability in all relevant states of charge as well as solubility. In particular, we highlight the design, synthesis, and electrochemical analysis of organic redox couples. Results will be presented on the cycling of phenothiazine and naphthoquinone derivatives in flowing full cell battery prototypes.