Subscribe Share Full episode and show notes Vulnerability Management , Breach , Phishing Beyond the AI Hype, Cyber Readiness in the Age of AI – Gibb Witham – SWN #595 I talk to Gibb Witham, President of Hack The Box, about cyber readiness, hands-on security training, Hack The Box, and AI in cybersecurity. July 3, 2026 Full Segment Notes I talk to Gibb Witham, President of Hack The Box, about cyber readiness, hands-on security training, Hack The Box, and AI in cybersecurity. Guest Gibb Witham President at Hack The Box Gibb Witham is President of Hack The Box. With two decades of experience across cybersecurity, AI, and enterprise software, Gibb has spent his career at the intersection of innovation, capital, and operational execution. Prior to Hack The Box, he spent 14 years as a venture capital investor at Paladin Capital Group, where he partnered with high-growth companies at the forefront of cybersecurity and enterprise AI innovation. His portfolio experience includes multiple companies growing from early stage to category leaders with over $100M in annual recurring revenue, with several successful IPOs and strategic acquisitions. Earlier in his career, Gibb led initiatives at IBM to build and scale its cloud and SaaS businesses in major industry verticals, following work as a strategy consultant advising Fortune 500 technology companies. Gibb holds a B.S. from Columbia University and lives with his family in Brooklyn, New York. Host Doug White https://securedigitallife.com/ Show More Stay in the Know, No Smoke and Mirrors – Join Our Newsletter Get expert insights and technical breakdowns straight to your inbox. Join Now Related Segments Vulnerability Management AI Cocaine Recipes, Russian Hack, Scattered Spider, Cisco, Amazon Q – Aaran Leyland – SWN #594 AI/ML Fixing pentesting, Meta is destroying its engineering org, the weekly news – Adriel Desautels – ESW #465 Vulnerability Management AI Brain Harvest, Fortibleed, Win 10, Blacksite, Windchill, Cisco, BB-8, Josh Marpet – SWN #593 Related Content Vulnerability Management The context gap: Building trusted agents in the age of AI-accelerated exploitation Vulnerability Management CISA adds SharePoint flaw to known exploited vulnerabilities list MSSP Intruder adds free exposure management plan for lean security teams You can skip this ad in 5 seconds