On this episode of CISO Tradecraft, host G Mark Hardy talks with Gary Hayslip about cybersecurity career growth beyond the traditional CISO “apex,” drawing on Hayslip’s 25+ years across military service, US Navy civil service, the City of San Diego as its first CISO, Webroot (CISO/CIO), SoftBank (including cyber and physical security), and most recently a field CISO role before being laid off. They discuss how the CISO role is evolving into merged executive positions (technology, risk, and AI), why continuous learning is essential as security changes rapidly, and why humans remain accountable even as AI reshapes teams. Hayslip outlines alternative paths like field CISO, data center security leadership, and VC/PE operating partner roles, and shares practical ways organizations used AI to speed legal review and automate security reporting while hig ...