Gary Hayslip: The Evolution of the Modern Field CISO

Welcome back to Zero Signal! In this episode, hosts Conor Sherman and Stuart Mitchell sit down with industry veteran Gary Hayslip. Currently serving as the Field CISO at Zenity and author of the CISO Desk Reference Guide, Gary brings decades of leadership experience spanning the U.S. Navy, municipal government, global tech firms like Webroot, and managing cyber risk across 500+ portfolio companies as the former Global CISO for SoftBank Investment Advisors. Gary breaks down how the CISO role is rapidly evolving into a business executive function that requires deep cross-departmental partnership, flexibility, and curiosity over rigid "no's." The discussion dives into the realities of the agentic transformation—exploring how AI is driving security into every business unit, why non-human identities and agents are becoming prime targets for social engineering, and why traditional SIEMs and SOCs must adapt to real-time automated decision-making. Gary also reflects on his journey from Navy Chief Petty Officer to boardroom leader, sharing his core philosophy on mentorship, writing for the community, and leaving the industry better than he found it. About the Guest Gary Hayslip is the Field CISO at Zenity, co-author of the CISO Desk Reference Guide series, and a retired U.S. Navy Chief Petty Officer. He has previously served as Global CISO for SoftBank Investment Advisors, CISO & CIO for Webroot, and CISO for the City of San Diego. Key Moments The Evolution of the Modern CISO: From Security Operator to Business Executive Managing Cyber Risk Across 500+ SoftBank Portfolio Companies The Field CISO Role: Strategy, Customer Advocacy, and Go-To-Market Alignment AI Governance & Non-Human Identity: Securing Agents and Enforcing Guardrails Meet our Sponsors Hampton North is the premier US-based cybersecurity search firm: https://hamptonnorth.com/?utm_source=... Sysdig is the leader in AI-powered real-time cloud defense: https://www.sysdig.com/?utm_source=we... RISCPoint Security & compliance consulting tailored to your business: https://www.riscpoint.com/