Cyber and the NY Giants

CISOs are accountable for cyber risk—but do they have the authority to change it?In this episode of Cloud Security Today, Matt sits down with cybersecurity researcher Raghav Singh to explore how organizational culture, power dynamics, and emerging AI capabilities shape security outcomes. Drawing on a burnout study involving 37 CISOs, Raghav explains how resource constraints and communication challenges reinforce one another—and why experience doesn’t necessarily make the job less stressful.They discuss why reporting to the CEO doesn’t guarantee influence, how AI could replace alert fatigue with the burden of explaining machine-generated judgments, and emerging research into how attacks take shape before execution.The conversation closes with three practical actions: align accountability with authority, address recurring organizational friction, and examine incidents as connected sequences of behavior rather than isolated alerts.

AI security has a hype problem.Every week brings a new headline about agents escaping sandboxes, AI replacing security teams, or models becoming “too smart” to control. But the more useful question for CISOs is much more practical: where do the actual security controls belong?In this episode, I sit down with Diana Kelley, CISO at Noma Security and one of the clearest voices in AI security, to separate AI mythology from operational reality.Diana explains why the LLM itself is not the security boundary, why the “harness” around the model matters, and how security teams should think about contamination, consequence, and runtime control as agentic AI moves into the enterprise.This conversation is not about AI hype. It is about what CISOs, security architects, and technical leaders need to understand before AI systems start taking autonomous action at machine speed.What You’ll LearnWhy AI security is different from traditional AppSecWhat an AI “harness” is and why it mattersWhy the LLM should not be treated as a security controlHow prompt injection relates to trust boundaries and context windowsWhy agentic AI increases both speed and consequenceKey TakeawaysThe model is not the control point.The LLM is powerful, but it is not deterministic enough to serve as the primary security boundary. Security controls need to live before and after inference — in the harness, surrounding software, workflow, and runtime environment.Think in terms of contamination and consequence.Contamination is what enters the context window. Consequence is what the system does after inference. Both need controls, especially when AI agents can act repeatedly and autonomously.Agentic AI changes the scale problem.A single bad prompt is one thing. Hundreds or thousands of agents looping through tasks at machine speed is another. The risk is not just bad output. It is autonomous action without adequate guardrails.

Christina Morillo shares her unconventional career journey from traditional IT to cybersecurity in the NFL, highlighting the importance of building trust, understanding business risk, and addressing misconceptions in cybersecurity.Christina's book: Zero Trust Networks

AI agents are moving from answering questions to taking action. That changes everything for identity and access management.In this episode, Ken Huang joins Matt to break down why traditional IAM was not built for agentic AI, where service accounts and OAuth scopes fall short, and what CISOs should do now to govern agents before they hit production at scale.Episode LinksKen's substackKen's paper from 2011 on AI (he was way ahead!)NIST AI RMF

In this episode, Michael Piacente shares insights on career transitions in IT and security, the evolving role of CISOs, and the impact of AI on security talent and practices. Discover how community, storytelling, and strategic hiring shape the future of cybersecurity leadership. ResourcesThe 2026 Global CISO Leadership ReportHitch PartnersNIST AI Framework

Send a textKelly Bissell shares his extensive experience in cybersecurity, from early internet security challenges to the transformative impact of AI and machine learning. Discover practical insights on risk management, organizational culture, and the future roles of cybersecurity professionals in an AI-driven world.Emerging AI Standardshttps://www.aiuc-1.com/https://cloudsecurityalliance.org/ai-safety-initiativeThe book Matt couldn't remember: https://www.amazon.com/Cuckoos-Egg-Tracking-Computer-Espionage/dp/0385249462

Send a textIn this conversation, Nicole Dove shares her unique journey into the cybersecurity field, highlighting her transition from a finance and audit background to becoming a leader in information security at Riot Games. She discusses the importance of continuous learning, the challenges of writing a book on cybersecurity, and the evolving role of Business Information Security Officers (BISOs) in aligning security with business goals. Nicole emphasizes the need for innovative problem-solving and relationship management in cybersecurity, while also reflecting on her personal routines for maintaining sharpness in her role.

Send a textIn this conversation, Rinki Sethi, a seasoned cybersecurity leader, shares her journey from being a CISO at major companies to her current role at Upwind Security. She discusses the evolving landscape of cybersecurity, the impact of AI, and the importance of community in the industry. Rinki emphasizes the need for strong communication skills for CISOs, the significance of evaluating company culture before taking on new roles, and the necessity of leveraging AI to enhance cybersecurity programs. She also highlights the importance of personal growth and building supportive networks within the cybersecurity community.

Send a textIn this month's installment, Toni De La Fuente shares his journey into cybersecurity, detailing his early experiences with computers and his passion for hacking. He discusses the creation of Prowler, an open-source cloud security tool, and its differences from commercial solutions. The conversation explores cloud security challenges, the importance of open-source solutions, and the dynamics of scaling a startup. Toni also emphasizes the significance of passion in one's career and offers advice for aspiring tech professionals.And yes...we also talk about his LOVE for Iron Maiden ;-)

Send a textIn this episode, Matt interviews Bel Lepe, CEO and co-founder of Cerby, discussing the challenges and opportunities in identity security. They explore the significance of disconnected applications, the impact of shadow IT, and the importance of automation and AI in enhancing security practices. Bel shares insights from his previous experience at Ooyala and the lessons learned in building Cerby, including the recent Series B funding and future plans for the company.TakeawaysDisconnected applications pose significant risks in identity management.Shadow IT is becoming a major part of the IT landscape, not just a side issue.The startup journey involves learning from past experiences and adapting strategies.The human element remains a critical factor in cybersecurity incidents.