Most breaches don’t happen because attackers are exceptionally clever. They happen because defenders are slow. This talk examines what modern attackers automate first and why those choices consistently outpace enterprise security programs built around alerts, approvals, and dashboards. Using real world attack patterns, we’ll show how adversaries scale initial access, rapidly map environments using legitimate tools, and time execution around defender hesitation. Aimed at both technical and executive audiences, this session challenges the industry’s obsession with detection over action and offers concrete guidance on shifting security programs toward speed, pre-authorized containment, and reducing blast radius before attackers make the next move.