From The SimSpace Summit 2026 – KB On The Go | Peter Lee and Ernie Ferraresso (Part 1)

In this episode of From The Field, recorded at DASH by Datadog in New York City, KB sits down with both of Datadog’s co-founders. First up is Olivier Pomel, Co-founder and CEO. He talks through the new security launches, including AI Guard and Bits AI for security, and explains why an observability background gave Datadog its right to win in security. He also covers why Datadog rebuilds acquisitions on its own platform instead of bolting them on, and why he expects security tooling to consolidate the way observability did. Then KB is joined by Alexis Lê-Quôc, Co-founder and CTO. He argues that AI has shrunk the gap between disclosure and exploit from weeks to hours. He explains why detection now has to be agentic, and why deciding which assets matter is still a human call. He also makes the case that lasting change comes from the teams on the ground.

KB sits down with Skip Mann, Lenovo’s Vice President of Enterprise Security Strategy, Assurance and Trust, to talk about how a company working across 180 markets and thousands of suppliers proves it can be trusted. They start with why nobody at that scale can verify everything, and why Skip says trust has to rest on evidence rather than assumptions. From there they get into why attackers don’t care how security teams are split up, and what customers should ask to see before trusting any vendor. KB asks how a company with deep roots in China handles government scrutiny, and Skip explains why Lenovo welcomes it, from the EU Cyber Resilience Act to repeated CFIUS reviews by the US government. They finish on supply chain resilience, how to do due diligence without drowning in scorecard tools, and the new trust questions AI is raising. About Skip: Skip Mann, Vice President, Enterprise Security Strategy, Assurance, & Trust Chief Security Office & Chief AI Office, Lenovo Skip Mann oversees four integrated functions – strategy and alignment, governance and assurance, trust and advocacy, and CSO operations – driving enterprise-wide security outcomes across Lenovo’s cyber, physical, supply chain, product, and responsible AI domains to advance resilience, regulatory alignment, and stakeholder trust. With more than 34 years in the security profession and 18 years in executive leadership, Skip is recognized as a thought leader in enterprise risk, organizational resilience, and security transformation. He is known for developing high performing teams and advancing converged, risk-informed security programs across global enterprises. Prior to joining Lenovo, Skip held senior roles within the US Department of Homeland Security and U.S. Department of Defense, including the US Army Headquarters in Washington D.C., United States Africa Command, United States European Command, and the Central United States Registry. Keywords: trust, assurance, supply chain security, supply chain resilience, third-party risk, due diligence, vendor risk management, GRC, certifications, NIST, ISO, EU Cyber Resilience Act, CRA, ENISA, EU AI Act, CFIUS, national security, geopolitics, converged security, physical security, operational resilience, Secure by Design, CISA, public-private partnership, coordinated vulnerability disclosure, AI governance, responsible AI, Lenovo, CISO, board, KBKast

KB sits down with Michael Pastor, Dean for Technology Law Programs at New York Law School and former General Counsel of New York City Cyber Command, to talk about who is accountable when AI gets it wrong. They start with Mythos-class tools and what they mean for the legal standard of reasonable security. Michael argues the test is effectiveness and what your people can validate, not cost, and that "I trusted the technology" won't survive discovery. From there they get into whether AI could help settle disputes between counterparties, how courts might handle highly technical cyber cases, and why Michael wants to retire the phrase "human in the loop" in favour of real oversight by people with context. They finish on contracts - what general counsel should demand from AI vendors now, why renewals are about to get harder, and why Michael is still optimistic about where it all lands. About Michael:Michael Pastor is a Professor of Law from Practice. He serves as New York Law School's Dean for Technology Law Programs, the Director of the James Tricarico Jr. Institute for the Business of Law and In-House Counsel, and Co-Director of the Innovation Center for Law and Technology. He teaches the In-House Counsel Experience Seminar and Drafting Contracts: Technology Transactions. Professor Pastor previously served as the General Counsel of the New York City Department of Information Technology and Telecommunications (DoITT) and the New York City Cyber Command (NYC3). Keywords: reasonable security, standard of care, AI liability, general counsel, legal counsel, technology contracts, AI vendor contracts, vendor management, audit rights, breach notification, human in the loop, human oversight, NYDFS, cybersecurity regulation, vulnerability management, Mythos, AI validation, contract renewal, privacy by design, security by design, New York City Cyber Command, CISO, board, KBKast

In the first weeks of March, Omar Santos got early access to the model that became Anthropic’s Mythos. About an hour of testing was enough to convince him cybersecurity had changed for good. Omar, a Distinguished Engineer in AI Security Engineering at Cisco and co-chair of the Coalition for Secure AI, says his bigger worry is how fast everyone else is catching up. Open weight models are closing in on the frontier labs, so attackers no longer need access to Mythos to find and exploit vulnerabilities. KB and Omar get into why Cisco won’t send a finding to engineering without proof of an active exploit, how a public open source fix gives attackers a ready-made recipe, and why a library a student abandoned years ago could be running inside your patient records system. Omar wants defenders to go further than finding and fixing faster. That means refactoring code, adding compensating controls, and turning the risk register from an annual exercise into something that runs continuously. About Omar: Omar Santos is a Distinguished Engineer at Cisco, focused on AI security, cybersecurity research, incident response and vulnerability disclosure. He co-chairs the Coalition for Secure AI (CoSAI) and the FIRST PSIRT Special Interest Group, sits on the board of OASIS Open, and chairs the OpenEoX and CSAF technical committees, where his work led to CSAF becoming an ISO standard. He also led the DEF CON Red Team Village for several years. Omar has written more than 25 books, 21 video courses and over 50 research papers, and holds multiple patents. Before Cisco, he served in the United States Marines. Keywords: Mythos, Anthropic, Project Glasswing, frontier AI, open weight models, AI security, AI in cybersecurity, vulnerability management, zero days, exploit development, open source security, software supply chain, SBOM, OpenEoX, CSAF, CodeGuard, Coalition for Secure AI, CoSAI, Cisco, compensating controls, eBPF, secure by design, zero trust, incident response, threat hunting, continuous assessment, risk register, GRC, CISO, board, KBKast

Most boards approved AI for the productivity gains, and far fewer asked what it would expose. Dean Saunders says conversations with large organisations usually start with models and end up on data: where it lives, who can reach it, and how quickly an agent can move it once staff have gone home. KB and Dean talk about shadow AI, approved tools used on personal accounts, and trusted apps that quietly add AI features without security knowing. They also get into why compliance keeps getting mistaken for security, and why regulators now want proof of what you did rather than the policies you wrote. About Dean: Dean Saunders is the Regional Director for Australia and New Zealand at Forcepoint, where he supports customers and partners in protecting sensitive data across modern cloud, SaaS and AI‑enabled environments. He focuses on expanding Forcepoint’s data security footprint in the region, helping security leaders strengthen visibility and control over high‑risk data through the company’s portfolio. With more than two decades of leadership experience in enterprise software, cybersecurity, SaaS, channel strategy and go‑to‑market execution across Australia and the broader Asia Pacific, Dean has built a strong track record driving regional growth. His background includes leading high‑performing sales teams, developing partner ecosystems and supporting technology organisations competing in complex markets. Before joining Forcepoint, Dean held senior commercial and leadership positions at Cyara, Forticode, Unitrends/Kaseya, Teradici, CommVault and Total Defense. His diverse experience spans direct sales, channel and alliances, partner‑led growth and strategic market development, complemented by advisory work focused on improving sales execution and market strategy. He holds an MBA from the University of the Sunshine Coast and has completed extensive professional development in enterprise selling, leadership, key account management and media training. Keywords: AI data security, data security posture management, agentic AI, shadow AI, data loss prevention, DLP, data discovery and classification, AI governance, compliance vs security, insider risk, Forcepoint, cyber risk, board cyber governance, KBKast