Board Priority But Lack of Access & CISO Pressure, 360 Privacy and Pentera Interviews - Chuck Randolph, Tom Pore - BSW #413

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Sep 17, 2025

Chuck Randolph, SVP of Strategic Intelligence & Security at 360 Privacy, shares his insights on the evolution of executive protection in the digital age. He highlights the shift from physical threats to online dangers, emphasizing the risks posed by data brokers and AI manipulation. Tom Pore, AVP of Sales Engineering at Pentera, discusses the rise of AI-driven cyberattacks and the need for proactive security strategies. Together, they advocate for a unified approach to risk management, addressing both cyber and physical security in an increasingly digital landscape.

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INSIGHT

Regulation Forces Boardroom Cyber Focus

NIS2 and DORA are elevating cybersecurity into boardroom priorities across Europe and critical sectors.
Organizations will weigh compliance costs against fines and may choose to self-insure when economics favor it.

INSIGHT

Board Access Is Necessary But Not Sufficient

Nearly half of CISOs report minimal or no access to full boards, which drives dissatisfaction and risk blind spots.
Board access alone isn't enough; CISOs must tailor communication to business metrics like revenue and churn.

ADVICE

Document Breach Impact And Materiality Decisions

Document breach impact findings and insist materiality decisions be made by executives or the board, not the CISO.
Get written CYA that records what you reported and who decided on disclosure to limit personal liability.

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In the leadership and communications segment, Lack of board access: The No. 1 factor for CISO dissatisfaction, Pressure on CISOs to stay silent about security incidents growing, The Secret to Building a High-Performing Team, and more!

Jackie McGuire sits down with Chuck Randolph, SVP of Strategic Intelligence & Security at 360 Privacy, for a gripping conversation about the evolution of executive protection in the digital age. With over 30 years of experience, Chuck shares how targeted violence has shifted from physical threats to online ideation—and why it now starts with a click.

From PII abuse to unregulated data brokers, generative AI manipulation, and real-world convergence of cyber and physical risks—this is a must-watch for CISOs, CSOs, CEOs, and anyone navigating modern threat landscapes. Hear real-world examples, including shocking stories of doxxing, AI-fueled radicalization, and the hidden dangers of digital exhaust.

Whether you're in cyber, physical security, or executive leadership, this interview lays out the urgent need for converged risk strategies, narrative control, and a new approach to duty of care in a remote-first world. Learn what every security leader needs to do now to protect key personnel, prevent exploitation, and build a unified, proactive risk posture.

This segment is sponsored by 360 Privacy. Learn how to integrate privacy and protective intelligence to get ahead of the next threat vector at https://securityweekly.com/360privacybh!

In this exclusive Black Hat 2025 interview, CyberRisk TV host Matt Alderman sits down with Tom Pore, AVP of Sales Engineering at Pentera, to dive into the rapidly evolving world of AI-driven cyberattacks. What’s happening?

Attackers are already using AI and LLMs to launch thousands of attacks per second—targeting modern web apps, exploiting PII, and bypassing traditional testing methods. Tom explains how automated AI payload generation, context-aware red teaming, and language/system-aware attack modeling are reshaping the security landscape. The twist? Pentera flips the script by empowering security teams to think like an attacker—using continuous, AI-powered penetration testing to uncover hidden risks before threat actors do. This includes finding hardcoded credentials, leveraging leaked identities, and pivoting across systems just like real adversaries.

To learn more about Pentera's proactive Ransomware testing please visit: https://securityweekly.com/penterabh

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Show Notes: https://securityweekly.com/bsw-413