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 highlighting cost, risk, and workforce concerns.

In this CISO Tradecraft episode, host G Mark Hardy interviews Steve McMichael, author of "How to Break into GRC: Mindset, Methods, and Skills," about entering cybersecurity through governance, risk, and compliance. McMichael shares his transition from accounting and explains GRC’s role as decision support and the interface between business and technical teams, breaking down governance, risk management, and compliance (including audits and third-party/supply-chain assurance). They discuss misconceptions that GRC is “just paperwork,” barriers like imposter syndrome, and strategies such as building T-shaped skills, targeting about 20% technical depth across domains, and developing credibility through a deep specialty. McMichael also describes an immersion mindset driven by emotional engagement, and showcases an open-source NIST Cybersecurity Framework Profile Assessment Database project on GitHub to help newcomers build skills and portfolio contributions.

Want to move from "security expert" to "trusted business leader"?

Join G. Mark Hardy and Michael Hammer. The mind behind the core of DMARC, for 40 years of hard-won wisdom on navigating the CISO role, This episode is a masterclass in evolving from a technical gatekeeper to a strategic influencer who changes the environment,.

Inside this episode:

• Modern Email Security: Why DMARC and SPF aren't "set and forget" tools and how to stop "cousin domain" attacks,.
• The 30-Minute Audit: Use the "Turn the Rocks Over" method to vet any vendor’s security posture in minutes.
• Risk vs. Ownership: Why you must ensure the executive team makes informed risk decisions, and why you should get them in writing.
• The AI Storm: How Mythos AI is accelerating the disclosure of years of hidden code vulnerabilities,.

Stop being a "compliance tax" and start protecting revenue. Watch now to learn how to build a true security culture