The America's Cup is the oldest sports trophy in the world but above all is a technology competition. It is a race against time to design, test, and deliver the fastest yacht on race day, with a team of Olympic-level athletes ready to sail it and make it fly thanks to cutting-edge hydrofoils. We will address these challenges with the current defenders of the Cup: Emirates Team New Zealand. We will discuss the important lessons learnt in optimizing human-machine workflows and some of the skills, mindset, and cultural shifts required to successfully embed AI technology into a fast-moving, performance-driven organization.