Ionic liquid crystals (ILCs) are a class of materials that are in the intersection of ionic liquids and liquid crystals. These materials typically consist of oppositely charged molecules with typically bulky ionic groups. Our work uses atomistic and coarse-grained molecular simulations to explore the behavior of a novel ILC lithium salt to explore its ion-conducting properties, and how these are mutually influenced by ion-pair binding, mesoscale structure and solvent inclusion. In particular, we analyze the relative mobility of Li+ ions and their larger counterions, and discuss the relevance of these results for the development of solid-state single-ion conducting materials for rechargeable batteries.