Tailwind ~ Ray Healy ~ Chief Revenue Officer w/ Chief Outsiders

Ray Healy joins Tailwind for a conversation on how prospecting has evolved from broad lead lists and high-volume cold calling into more targeted, intent-driven, multi-channel outreach. We talk about building lists around a clearly defined ICP and buying committee, starting higher in the organization when possible, using signals like regulatory issues and trade-group activity to identify companies with real problems to solve, and tailoring channel strategy based on deal size and sales complexity. We also cover how AI can make research and personalization far more efficient without replacing the human element, why sales teams should focus on a small number of meaningful KPIs instead of measuring everything, and how reducing administrative work can give sellers more time to actually sell.