Software touches every aspect of our lives, and no where is that clearer than in the automotive industry. With the recent surge to AI for self driving cars, we lose sight of adaptive cruise control, anti-lock breaks, and in-cab media centers that all require software to operate. However, did you realize that software plays a fundamental role in the streets you drive on? This talk is a post-mortem of a prototype system we built for optimizing the use of municipal funds for highway maintenance in the state of Indiana. While the optimizer is a central piece of the system, it wasn’t the whole system, or even the most challenging problem! In this talk, we’ll cover: * The general problem of highway maintenance * How users acceptance and understanding may be a more important metric than pure cost optimization * How to build AI in an agile manner * How AI was merely a part of a much larger system * What changes when your software has to change hearts and minds as well as accomplish a technical task?