Discover the psychology hack reshaping cybersecurity training. Learn how positive reinforcement, AI, and cyber literacy are driving a true training revolution in this episode of The Digital Shift.

In this episode, we sit down with Craig Taylor, Co-Founder & CEO of CyberHoot. With over 25 years of cybersecurity experience and leadership roles at CSC, JP Morgan Chase, and VistaPrint, Craig has dedicated his career to solving one of the biggest challenges in cybersecurity: the human firewall.

This conversation uncovers how CyberHoot scaled from 45,000 to 80,000 users in just 18 months, filed a patent for its positive reinforcement training methodology, and is leading the way with psychology-driven, gamified training to fight modern cyber threats. We also dive into industry trends, AI-driven phishing, ransomware evolution, and the company’s future growth plans with partnerships like AARP and AAA.

Craig Taylor is a Certified Information Systems Security Professional (CISSP) since 2001, and a 30-year veteran of Cybersecurity. In 2014 he co-founded a cybersecurity training company - CyberHoot - to bring positive reinforcement and Engagement back to cybersecurity training. During his career, Craig has led cybersecurity organizations in Online Services (@CSC), Finance (@JP Morgan Chase), and manufacturing (@Vistaprint). Additionally, Craig also leads a virtual CISO consulting service that delivers virtual Chief Information Security Officer (vCISO) services to more than 3o companies (all sizes and industries). Craig's passion project is cancer fundraising - he and his son have raised over 150k for cancer research by riding in the Pan Mass Challenge for the last 11 years.

Key highlights from this episode:

📊 Positive reinforcement training vs. traditional phishing tests

🔒 Why weak passwords and human errors cause most breaches

🚀 How AI is fueling more sophisticated cyberattacks

💼 Partnerships with MSPs, universities, and large organizations

🌍 Growth strategies through gamification and global expansion

⚠️ Customer retention and acquisition challenges in cybersecurity

If you’re a business leader, IT professional, or cybersecurity enthusiast, this episode offers powerful insights on how to strengthen your defenses and build a culture of security.

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🧑 Today's Guest Information:

LinkedIn: https://www.linkedin.com/in/craigmtaylor/

Website: https://cyberhoot.com/

Timestamps: 00:00 - Pre-Interview Setup

08:58 - Company Background & Founding Story

16:10 - Psychology-Driven Training Methodology

25:59 - Industry Trends & Threat Landscape

41:51 - Current Business Success Factors

43:34 - Growth Challenges & Retention Strategy

55:26 - Future Growth Plans & Vision

01:02:36 - Post-Interview Business Discussion & Outro Surprise

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