This case study details the collaboration between Pythian and Day & Ross, a major North American transportation and logistics firm, to enhance freight throughput and scalability through the implementation of Google Gemini Generative AI. The study outlines the challenges faced by Day & Ross, particularly the need for real-time data visibility and accuracy in their Transportation Management System (TMS). It describes how manual data entry of Bills of Lading (BOLs) was causing delays and backlogs, prompting the need for an innovative solution. Pythian proposed an automated data extraction system utilizing Google Cloud Platform and Gemini 1.5 Pro, which significantly reduced manual processing time and improved operational efficiency. The implementation led to faster unloading of freight, enhanced customer visibility, and a streamlined workflow. The case study concludes with the positive outcomes of the project, including improved data accuracy and the ability to meet shipping commitments, showcasing the effectiveness of AI in transforming logistics operations.