Building the Professional CISO: Gary Hayslip on Merging Risk, IT, and Business

The Professional CISO

In this episode, David Malicoat interviews Gary Hayslip, Global Chief Information Security Officer (CISO) at SoftBank Investment Advisors. Gary shares his deep insights on the evolution of the CISO role, discussing how it’s becoming more integrated with risk management, business strategy, and AI. He reflects on his own career journey from the U.S. Navy to becoming a global cybersecurity leader, offers practical advice for veterans transitioning into cyber roles, and explores how the future of cybersecurity leadership is shaping up.

Whether you’re an aspiring CISO, a cybersecurity professional, or a business leader, this episode is packed with actionable insights and advice from one of the most respected figures in the industry.

Key Topics Discussed:

• Gary Hayslip’s Journey: From military service to global cybersecurity leadership.

• Professionalizing the CISO Role: Why the CISO role is evolving and how it’s merging with other business and risk functions.

• CISO Tenure and Burnout: Understanding why CISO tenures often range from 18 to 36 months and the factors behind this.

• Advice for Veterans Transitioning to Cybersecurity: Gary shares how veterans can prepare for civilian cyber roles and why cyber offers a “mission-driven” career.

• The Future of the CISO Role: AI, risk management, product security, and why the CISO’s responsibilities are expanding.

Key Quotes from Gary Hayslip:

• “Cyber is a discipline made up of multiple domains. The CISO role is the lead executive within cyber, but it’s something you grow into over time.”

• “I see the CISO role merging with other risk executive roles. We’re business executives managing risk using technology, people, and processes.”

• “AI isn’t something to run from. It’s something you figure out how to use and protect. If you do it right, you’ll be effective. If you screw it up, it’s a resume-generating event.”

Guest Bio:

Gary Hayslip is the Global Chief Information Security Officer (CISO) at SoftBank Investment Advisors, a cybersecurity veteran with decades of experience in the U.S. Navy, municipal government, cybersecurity product advisory roles, and venture capital. He’s also a co-author of the CISO Desk Reference book series and an influential thought leader in the cybersecurity industry.

Connect with Gary Hayslip:

• LinkedIn: https://www.linkedin.com/in/ghayslip/

• Twitter: https://x.com/ghayslip

Episode Resources:

• CISO Desk Reference Guide: Volume 1 & 2 by Gary Hayslip and co-authors Bill Bonney and Matt Stamper

• Cloud Guru (for cloud certifications)

• Udemy Python Courses (for learning scripting)

Additional Links:

• Subscribe to The Professional CISO Show on Spotify and Apple Podcasts

• Follow us on YouTube: www.youtube.com/@TheProfessionalCISO

• Join the conversation on LinkedIn: The Professional CISO LinkedIn

Chapters:

• 0:00 - Intro to Gary Hayslip

• 1:30 - Gary’s Cybersecurity Journey

• 5:00 - Professionalizing the CISO Role

• 14:00 - CISO Tenure and Burnout

• 19:00 - Advice for Veterans in Cybersecurity

• 23:00 - The Future of the CISO Role

• 29:00 - 10 Questions with Gary Hayslip

• 33:00 - Closing Thoughts on Cyber Leadership

Call to Action:

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