The early diverging, dolphin-sized, cetacean clade Xenorophidae are a short-lived radiation of toothed whales (Odontoceti) that independently evolved two features long thought to be odontocete synapomorphies: the craniofacial and cochlear morphology underlying echolocation and retrograde cranial telescoping (i.e., posterior migration of the viscerocranium). This family was based on Xenorophus sloanii, which, for the past century, has been known only by a partial skull lacking a braincase and tympanoperiotics, collected around 1900 from the Ashley Formation (28–29 Ma, Rupelian) near Ladson, South Carolina. A large collection of new skulls and skeletons (ChM PV 5022, 7677; CCNHM 104, 168, 1077, 5995) from the Ashley Formation considerably expands the hypodigm for this species, now the best known of any stem odontocete and permitting evaluation of intraspecific variation and ontogenetic changes. This collection reveals that the holotype (USNM 11049) is a juvenile. Xenorophus sloanii is a relatively large odontocete (70–74 cm CBL; BZW = 29–31 cm; estimated body length 2.6–3 m) with a moderately long rostrum (RPI = 2.5), marked heterodonty, limited polydonty (13–14 teeth), prominent sagittal crest and intertemporal constriction, and drastically larger brain size than basilosaurid archaeocetes (EQ = 2.9). Dental morphology, thickened cementum, a dorsoventrally robust rostrum, and thick rugose enamel suggest raptorial feeding; oral pathology indicates traumatic tooth loss associated with mechanically risky predation attempts. Ontogenetic changes include increased palatal vomer exposure; fusion of the nasofrontal, occipito-parietal, and median frontal sutures; anterior lengthening of the nasals; elaboration of the nuchal crests; and blunting and thickening of the antorbital process. The consistent deviation of the rostrum 2–5° to the left and asymmetry of the palate, dentition, neurocranium, mandibles, and vertebrae in multiple specimens of Xenorophus sloanii suggest novel adaptations for directional hearing driven by the asymmetrically oriented pan bones of the mandibles. A second collection consisting of a skeleton and several skulls from the overlying Chandler Bridge Formation (24–23 Ma, Chattian) represents a new species, Xenorophus simplicidens n. sp., differing from Xenorophus sloanii in possessing shorter nasals, anteroposteriorly shorter supraorbital processes of the frontal, and teeth with fewer accessory cusps and less rugose enamel. Phylogenetic analysis supports monophyly of Xenorophus, with specimens of Xenorophus simplicidens nested within paraphyletic X. sloanii; in concert with stratigraphic data, these results support the interpretation of these species as part of an anagenetic lineage. New clade names are provided for the sister taxon to Xenorophidae (Ambyloccipita), and the odontocete clade excluding Xenorophidae, Ashleycetus, Mirocetus, and Simocetidae (Stegoceti). Analyses of tooth size, body size, temporal fossa length, orbit morphology, and the rostral proportion index, prompted by well-preserved remains of Xenorophus, provide insight into the early evolution of Odontoceti.