What Makes a Great CISO? A Playbook from Gary Hayslip

What separates a great CISO from a great one? In this powerhouse conversation, Ron invites friend and cybersecurity leader Gary Hayslip, CISO at SoftBank Investment Advisers, back on the mic to discuss what it takes to lead in today’s high-stakes digital world. Gary shares battle-tested insights on accountability, the evolving expectations of the CISO role, and how AI is reshaping leadership without replacing it.

Gary shares stories ranging from military mishaps to enterprise-scale transformation, and makes the case for visibility, trust, and embracing change. His perspective brings clarity to the fundamental responsibilities of a CISO and the mindset required to lead with impact.

Impactful Moments

00:00 – Introduction

02:00 – Defining the modern CISO as a business leader

05:45 – Why CISOs should never delegate accountability

07:30 – The danger of staying invisible

10:45 – The $40K UPS explosion mistake

15:00 – How leaders build trust in new teams

19:10 – Visibility is not micromanagement

24:30 – Staying humble while leading big

30:00 – Building “Rocky the Raccoon” internal GPT

34:30 – Hiring for AI fluency in security teams

Links:

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