As industries become more connected, and 5G services become increasingly embedded in enterprises, there needs to be a continued evolution both in the telcos and the enterprises they serve. CSPs need to continue to evolve their systems, automating their networks and the processes that enable different use cases and quick adaptation. Additionally, they must have the right commercial and technical teams in place to assist clients and address issues. On the other hand, the digital transformation experienced by enterprises has led to an important shift in the talent and skillsets needed to build out and maintain integrated cellular services in the enterprise. How far have we come in adapting to the digital and connected enterprise? What are some important organizational and cultural shifts necessary to deliver the much discussed but rarely seen fully connected enterprise?