
Cybersecurity Is a Leadership Problem, Not an IT Problem
From Winners Circle With Jay by Jay Adewole
May 27, 2026 · 29 min · Season 5 · Episode 18
About this episode
This episode discusses how cybersecurity is a leadership responsibility rather than just an IT issue.
Cybersecurity breaches don’t happen because technology fails—they happen when leadership fails to take ownership of risk . In this powerful episode of The Winners Circle Podcast , host Jay Adewole sits down with Orloff Phillips , a Chief Information Officer and strategic technology enablement advisor with over 20 years of experience across cybersecurity governance, AI adoption, and emerging technologies including quantum computing. Orloff has advised boards and executive leadership teams across higher education, nonprofits, municipal systems, and enterprise organizations—helping leaders align technology decisions with business objectives, regulatory requirements, and long-term organizational resilience. Born in Georgetown, Guyana, he brings a global perspective and disciplined leadership lens to today’s most complex digital risks. This episode challenges a dangerous misconception many organizations still hold: that cybersecurity belongs solely to IT. Together, Jay and Orloff explore why cybersecurity is fundamentally an enterprise and leadership responsibility , how governance matters more than tools, and what executives and board members should actually be asking about risk…
People in this episode
Host: Jay Adewole
Guest: Orloff Phillips
Topics covered
- cybersecurity
- leadership
- risk management
- governance
- technology
- organizational resilience
Keywords
- cybersecurity
- leadership
- risk
- governance
- compliance
- organizational resilience
- technology decisions
Mentioned in this episode
Organizations: NIST, IS
Places: Georgetown, Guyana
More episodes of Winners Circle With Jay
- The Hidden Power of Authenticity in a World Obsessed with AI and Homogeneity · June 10, 2026 · 38 min
- How Entrepreneurs Can Stay Relevant When AI Reshapes Visibility and Customer Acquisition · June 3, 2026 · 52 min
- Building Better Cultures: The Hidden Engine Behind Business Success · May 20, 2026 · 50 min
- “The Resilient Leader’s Mindset: Practical Steps to Transform Disruption into Opportunity.” · May 13, 2026 · 42 min
- Transformational Leadership in the Modern Workplace · May 6, 2026 · 47 min
- The Wealth Dilemma: Should You Invest in Stocks or Real Estate?’ · April 29, 2026 · 40 min
Explore listener stats, chart rankings, contacts and more on the Winners Circle With Jay podcast page.