The 2025–2026 CTV Playbook — From Shoppable TV to Scene-Level Targeting from Windsail Partners examines how connected TV is evolving from broad household targeting into a more interactive, context-aware, and performance-driven channel. As platforms such as Amazon, Roku, Walmart Connect, and NBCUniversal expand shoppable ad formats, QR-enabled experiences, and direct-to-checkout integrations, CTV is increasingly bridging brand and commerce outcomes. At the same time, advances in scene-level and contextual targeting — enabled by technologies such as automatic content recognition (ACR), AI-driven metadata, and object-level video analysis — are being driven by data and measurement leaders including Innovid, TVision, Samba TV, Nielsen, and LiveRamp. Together with DSPs like The Trade Desk and Google, these players are redefining how relevance, attribution, and engagement are delivered in streaming environments. This report outlines how the convergence of commerce, content intelligence, and privacy-safe data is reshaping advertiser expectations — and why these capabilities are becoming central to CTV strategy, partnerships, and M&A activity.