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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 Links Ken'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. Resources The 2026 Global CISO Leadership Report Hitch Partners NIST AI Framework

Send a text Kelly 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 Standards https://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 text In 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 text In 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 text In 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 text In 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. Takeaways Disconnected 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.

Send a text In this conversation, Tammy Klotz discusses her journey as a leader and author, focusing on her book 'Leading with Empathy and Grace.' She shares insights on the importance of empathy, vulnerability, and authenticity in leadership and the challenges and rewards of writing a book. The discussion highlights the significance of acknowledging personal lives in the workplace and the foundational role of trust in professional relationships. If you are an aspiring leader in Cyber, this episode is for you. Tammy shares her secrets to successful leadership.

Send a text In this conversation, MK Palmore shares insights from his diverse leadership journey, spanning the Marine Corps, FBI, and cybersecurity. He emphasizes the importance of a people-centered leadership approach, the balance between technical and leadership skills, and the significance of effective communication. MK reflects on his experiences, the impact of mentorship, and the lessons learned from both successes and failures in leadership roles. MK highlights the challenges in attracting diverse talent to cybersecurity and the necessity of nurturing new professionals. He concludes with insights on continuous learning and the importance of maintaining a beginner's mindset. Takeaways Diverse experiences shape leadership philosophy.Mentorship plays a significant role in professional development.Silence from leaders can lead to assumptions and uncertainty.Leaders should increase communication during times of uncertainty.Maintaining a mindset of continuous learning is vital for personal growth.Chapters 00:00 Introduction to Leadership and Music 02:57 Diverse Leadership Experiences 06:05 The Importance of People-Centered Leadership 09:05 Technical Skills vs. Leadership Skills 11:49 Communication as a Leadership Skill 14:53 Learning from Mistakes in Communication 18:01 The Impact of Silence in Leadership 20:44 Navigating Uncertainty in Leadership 25:06 Bridging the Gap: Technical and Business Communication 30:22 Building Personal Brand and Eminence 32:53 Overcoming Barriers in Cybersecurity Talent Acquisition 38:31 Staying Sharp: Continuous Learning and Adaptability

Send a text In this conversation, Lance Spitzner shares his unique journey from a military tank officer to a pioneer in cybersecurity, detailing the evolution of his career and the inception of the Honeynet Project. He emphasizes the importance of understanding the human element in security, advocating for a shift from mere security awareness to fostering a robust security culture within organizations. Spitzner discusses practical steps for security teams to enhance their approach, including leveraging AI to improve communication and engagement. He concludes by reflecting on the impact of his work and the growing recognition of the human side of cybersecurity. Takeaways The Honeynet Project was born from a need for cyber threat intelligence.Security culture is broader than security awareness; it encompasses attitudes and beliefs.Changing the environment is key to changing organizational culture.AI can be leveraged to enhance communication and simplify security policies.Positive interactions with security teams build a stronger security culture.Chapters 00:00 From Military to Cybersecurity Pioneer 03:04 The Birth of the Honeynet Project 05:59 Understanding the Human Element in Security 09:13 Security Culture vs. Security Awareness 11:51 Changing Organizational Culture for Security 14:46 Practical Steps for Security Teams 17:55 Leveraging AI in Security Culture 21:11 Measuring Success in Cybersecurity Training

Send a text In this conversation, Dr. Chase Cunningham, aka Dr. Zero Trust, shares his unique journey into the cybersecurity field, emphasizing the importance of purpose and self-care in a high-stress industry. He discusses the challenges of implementing zero trust strategies in organizations, the significance of understanding offensive tactics to enhance defensive measures, and the need for systemic change in national cybersecurity. Dr. Zero Trust also provides valuable advice for aspiring cybersecurity professionals, highlighting the supportive community and the importance of continuous learning. Takeaways Zero Trust is a strategy, not a product.Self-care is critical in high-stress environments.Understanding offensive tactics is essential for defense.Start small when implementing Zero Trust.

Send a text In this conversation, Steve Martano discusses his journey from writing about baseball analytics to becoming a key player in cybersecurity executive search and strategy. He emphasizes the evolving role of CISOs, the importance of aligning with business objectives, and the need for strong leadership skills. The discussion also covers trends in CISO compensation, the mental health challenges faced by security leaders, and the significance of organizational culture in driving satisfaction and effectiveness in cybersecurity roles. The Latest CISO Compensation Trends & Benchmarks. Takeaways Understanding economics can enhance a CISO's effectiveness.Compensation data must be contextualized for accurate benchmarking.Low attrition doesn't always indicate job satisfaction.CISOs face increasing pressures and scope creep in their roles.The job market is expected to become more active in 2025. Chapters 00:00 The Journey from Baseball to Cybersecurity05:53 The Intersection of Leadership and Cybersecurity12:00 Mental Health and Satisfaction Among CISOs17:49 Preparing for Future Attrition in Cybersecurity Roles26:29 Engagement and Satisfaction Beyond Compensation32:13 The Evolving Role of Cybersecurity Leadership38:15 Mentorship and Professional Growth The future of cloud security. Simplify cloud security with Prisma Cloud, the Code to Cloud platform powered by Precision AI. Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.