As the concept of television continues to evolve, audiences have more options than ever when it comes to viewing premium content. While the ability to connect with consumers across screens is immensely valuable for publishers and advertisers alike, it has also become increasingly complex to insert ads anywhere content appears. Particularly, it is difficult to account for ad insertion challenges, while also honoring the business rules of a deal and delivering an optimal user experience. Several forces are at play here: (1) many endpoints have strict player requirements, (2) advertisers/agencies often have difficulty meeting these technical specifications, and (3) premium publishers struggle to fill inventory requirements for multiple endpoints in a way that maximizes sell-through. These factors are costing buyers and sellers numerous ad dollars from missed revenue opportunities.