Offensive Security practitioners have a wide array of tools and tactics to breach perimeters, bypass controls, and hack the planet. Security Engagement has the devices to influence in a scalable and repeatable way. Yet somehow our efforts to enact change in the world around us are often abated by organizational positioning, cognitive biases, and public misunderstanding. In this talk we explore where the boundaries for these teams at internal organizations could be expanded, strategies for obtaining buy in, and how strategic partnerships can amplify security behavior change at scale. Drawing on experience from the front lines, tangible solutions for implementation and measurement of impact will be presented.