The Cybersecurity Blind Spot Leaders Are Missing, and Why It’s About to Get Worse

The Cybersecurity Blind Spot Leaders Are Missing, and Why It’s About to Get Worse

May 13, 2026 · 41 min · Season 1 · Episode 121

About this episode

The episode discusses the disconnect in enterprise cybersecurity and the reasons behind increasing breaches despite higher security spending.

Podcast: The Security Strategist Guest: Garrett Hamilton, CEO , Reach Security , and Jay Wilson, CIO & CISO, Insurity Host: Shubhangi Dua, Podcast Producer and B2B Tech Journalist , EM360Tech There’s a growing disconnect at the core of enterprise cybersecurity, and most enterprise leadership teams don’t recognise it yet. With budgets increasing, tools improving more than ever, and AI quickly being integrated into both offensive and defensive strategies. On paper, this should be a golden era for cyber resilience. However, many enterprises feel more exposed, not less. The issue isn’t a lack of innovation, rather it’s something harder to see—and far more dangerous. In this episode of The Security Strategist podcast , host Shubhangi Dua, Podcast Producer and B2B Tech Journalist at EM360Tech, sits down with Garrett Hamilton, CEO of Reach Security , and Reach customer, Jay Wilson, CIO & CISO at Insurity . They unpack why enterprises are still getting breached despite record security spend—and how configuration drift , AI-driven threats, and operational blind spots are quietly reshaping the future of cyber defence. They address the key issues enterprises are playing with in the…

People in this episode

Host: Shubhangi Dua

Guests: Garrett Hamilton, Jay Wilson

Topics covered

Mentioned in this episode

Organizations: Reach Security, Insurity

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