AI insider threats and misconfigurations are redefining cybersecurity’s front lines. Discover how artificial intelligence, weak password habits, and global hiring scams are fueling the next wave of digital breaches in this episode of The Digital Shift.

In this conversation, we sit down with Jerry Chappee, Co-Founder & CTO of Eagle Global Cybersecurity, a leader in red teaming, compliance scanning, and AI-driven security defense. With decades of cybersecurity experience and multiple certifications (MBA, C|CISO, CISSP, CBCP), Jerry shares powerful insights into how insider threats, AI misuse, and password negligence collide to create the perfect cyberstorm.

Key highlights from this episode:

🔒 North Korean hackers using AI to fake job interviews and steal IP

🧠 How AI is transforming red teaming and compliance scanning

⚙️ Misconfiguration & password hygiene: the twin pillars of risk

📊 The growing threat to municipalities and hospitals worldwide

🧰 AWS-based red teaming and phishing simulation tactics

🚀 How Eagle Cybersecurity helps clients harden their defenses

📞 Real-world advice for password management and access control

🌍 Expanding cybersecurity compliance in U.S. and EU markets

If you’re an IT leader, cybersecurity professional, or business owner concerned about insider risks and AI-driven attacks, this episode is a must-watch.

🔔 Subscribe to The Digital Shift for more conversations on innovation, AI, and cybersecurity.

👉 Subscribe: https://www.youtube.com/@DigitalShiftOfficial?sub_confirmation=1

🏫 Skool: Become an automation expert → https://www.skool.com/smooth-automation-1830

👤 Guest Information:

LinkedIn: https://www.linkedin.com/in/jerry-chappee-mba-c-ciso-cissp-cbcp-0341bb2/

Website: https://eaglecybersecurity.com/

⏱ Timestamps

00:00 - AI-Powered Insider Threats

06:42 - Misconfiguration & Password Hygiene

11:38 - Passphrases & Rotation Best Practices

16:27 - AI Integration in Cybersecurity

18:22 - Red Teaming & Compliance Scripting

24:20 - AWS for Penetration Testing

27:22 - Targeting California Municipalities

29:22 - Hospital Security & GDPR Compliance

31:49 - Least Privilege & Access Control

33:27 - Documentation for NIST & ISO Standards

34:05 - User Training & Phishing Prevention

35:40 - Outsourcing for Small Businesses

39:14 - Municipal Approval & Scope Challenges

40:44 - Disaster Recovery & Business Continuity

41:55 - Final Security Advice

#TheDigitalShift #Cybersecurity #AI #InsiderThreats #CyberDefense #DataProtection #RedTeam #PenetrationTesting #PasswordSecurity #NetworkSecurity #CyberAwareness #CloudSecurity #EthicalHacking #RiskManagement #Compliance #CyberAttack #AIinCybersecurity #DigitalTransformation #InformationSecurity #TechPodcast