As a full-blown research topic, numerical cognition is investigated by a variety of disciplines including cognitive science, developmental and educational psychology, linguistics, anthropology and, more recently, biology and neuroscience. However, despite the great progress achieved by such a broad and diversified scientific inquiry, we are still lacking a comprehensive theory that could explain how numerical concepts are learned by the human brain. In this perspective, I argue that computer simulation should have a primary role in filling this gap because it allows identifying the finer-grained computational mechanisms underlying complex behavior and cognition. Modeling efforts will be most effective if carried out at cross-disciplinary intersections, as attested by the recent success in simulating human cognition using techniques developed in the fields of artificial intelligence and machine learning. In this respect, deep learning models have provided valuable insights into our most basic quantification abilities, showing how numerosity perception could emerge in multi-layered neural networks that learn the statistical structure of their visual environment. Nevertheless, this modeling approach has not yet scaled to more sophisticated cognitive skills that are foundational to higherlevel mathematical thinking, such as those involving the use of symbolic numbers and arithmetic principles. I will discuss promising directions to push deep learning into this uncharted territory. If successful, such endeavor would allow simulating the acquisition of numerical concepts in its full complexity, guiding empirical investigation on the richest soil and possibly offering far-reaching implications for educational practice.