The Road to Accountable AI

Walter Haydock draws a direct line from military risk management to the enterprise AI challenge. His argues that organizations need to stop doing "math with colors," and move toward quantitative assessment that assigns dollar values to potential AI failures. Much of the conversation in this episode focuses on ISO 42001, the global standard for AI management systems, which Haydock has championed and which his own firm has gone through. He draws a three-part taxonomy of AI governance frameworks: legislation you either comply with or don't, voluntary self-attestable frameworks like the NIST AI RMF, and externally certifiable standards like ISO 42001 that bring independent verification. Haydock outlines a forward-looking vision in which certification, insurance, and legal safe harbors reinforce one another. Machine-readable audit data will eventually allow insurers to make informed underwriting decisions about AI risk, reducing uncertainty for both enterprises and their customers. Though, as he acknowledges, we are still far from that environment, with AI audits today still roughly 90% manual. Walter Haydock is the founder of StackAware, which helps AI-powered companies manage security, compliance, and privacy risk. Before entering the private sector, he served as a reconnaissance and intelligence officer in the U.S. Marine Corps, as a professional staff member for the Homeland Security Committee of the U.S. House of Representatives, and as an analyst at the National Counterterrorism Center. He is a graduate of the United States Naval Academy, Georgetown University's School of Foreign Service, and Harvard Business School. Transcript Deploy Securely (Haydock's Substack)

Richa Kaul breaks down the AI risk landscape for enterprises, and argues that the key to managing all of them is resisting the urge to sensationalize. Kaul offers a candid assessment of where enterprise AI governance committees are falling short, noting that many lack the technical fluency to ask vendors the right questions, such as where customer data goes, whether it trains other clients' models, and what specific steps reduce hallucination. She suggests that market-driven security standards like SOC-2 and ISO 27001 often matter more in practice than government regulation, creating a "beautiful ecosystem" where risk management runs ahead of the law. Looking forward, she addresses the growing challenge of agentic AI systems that make decisions autonomously, offering a deceptively simple prescription: Map every action an agent can take, know where your highest risk sits, identify the critical decision points, and demand human sign-off at each one/ Richa Kaul is the founder and CEO of Complyance, an AI-native enterprise governance, risk, and compliance (GRC) platform. Before founding Complyance, she was Chief Strategy Officer at ContractPodAi, a legal technology company, and previously served as Managing Director at the Virginia Economic Development Partnership and as a management consultant at McKinsey. Transcript Complyance Raises $20M to Help Companies Manage Risk and Compliance (TechCrunch, February 11, 2026)

How AI is, could, and shouldn't be used in military and other national security contexts is a topic of growing importance. Recent conflicts on the battlefield, and between the U.S. military and a major AI lab, are forcing conversations about legal, ethical, and appropriate business limitations for increasingly powerful AI tools. Michael Horowitz, a Political Science professor and Director of Perry World House at the University of Pennsylvania, is one of the world's leading experts on military AI and autonomous weapons. In this episode, drawing on his two stints in the U.S. Department of Defense, Horowitz walks through the major buckets of military AI use. He explains why militaries are, in some ways, more incentivized than any other institution to get AI governance right, but genuine tensions among speed, effectiveness, and meaningful human control can make responsible military AI difficult in practice. We cover Anthropic's recent dispute with the Pentagon as a case study in the fragile and increasingly consequential relationship between Silicon Valley and the defense establishment. Michael C. Horowitz is the Richard Perry Professor of Political Science and Director of Perry World House at the University of Pennsylvania, and a Senior Fellow for Technology and Innovation at the Council on Foreign Relations. From 2022 to 2024, he served as U.S. Deputy Assistant Secretary of Defense for Force Development and Emerging Capabilities, where he was the principal author of the U.S. Political Declaration on Responsible Military Use of AI and Autonomy. He is the author of The Diffusion of Military Power: Causes and Consequences for International Politics and co-author of Why Leaders Fight. Transcript Battles of Precise Mass: Technology Is Remaking War — and America Must Adapt (Foreign Affairs, 2024) The Ethics & Morality of Robotic Warfare: Assessing the Debate over Autonomous Weapons (Daedalus, 2016) Rules of Engagement (Penn Gazette, 2025)