This paper introduces the Telecommunication’s Industry approach to adopt Artificial Intelligence mechanisms into daily tasks and operations, in order to accelerate digital transformation. The scope of this paper is to analyze and explore the opportunities and the challenges that are raised for telecommunications organizations by exploiting vast amounts of data they own or handle. The opportunities and challenges that are created by AI technologies are presented through several Use Cases, that IT Innovation Center of OTE Group is investigating, and create the baseline towards digital transformation and the engagement in future markets. However, as depicted in this paper, although the numerous opportunities, telecoms in this AI journey face many challenges that they need to overcome. This work in progress is under the DataPorts project that is funded by the European Union’s Horizon 2020 Research and Innovation Programme under grant agreement No. 871493.