Episode 61: Reinventing Cyber Tabletop Exercises with AI: Den Jones & Cassio Goldschmidt

<p>This episode of <strong>“909 Exec,”</strong> hosted by 909 Cyber CEO Den Jones, explores where cybersecurity meets business strategy. Guest <strong>Cassio Goldschmidt</strong>, CTO of Reflex, discusses his career evolution and the launch of Reflex Security.</p><ul><li><p><strong>Early Tech Roots:</strong> Discovered computers as a teenager in Brazil, which naturally led to a computer science degree.</p></li><li><p><strong>Silicon Valley:</strong> Moved to California to join Cisco just before the internet boom.</p></li><li><p><strong>Initial Projects:</strong> Worked on industrial automation in Brazil, followed by PC configuration (“Splice”) and early video conferencing initiatives at Cisco.</p></li></ul><ul><li><p><strong>CISO Success:</strong> Effective Chief Information Security Officers (CISOs) need strong interpersonal skills and business alignment, not just technical expertise.</p></li><li><p><strong>Role Differences:</strong> A Business Information Security Officer (BISO) acts as a consultant across shared business units. In contrast, a CISO owns the resources and integrates deeply into daily operations.</p></li><li><p><strong>Community Networking:</strong> Engaging in communities like OWASP and BSides is essential for ongoing learning, collaboration, and building career resilience.</p></li></ul><ul><li><p><strong>A New Challenge:</strong> After guiding ServiceTitan&#39;s security program from its early days through an IPO, Cassio left his CISO role to satisfy his engineering and inventive mindset.</p></li><li><p><strong>Founding Reflex:</strong> He launched Reflex (Reflect Security) to build a truly innovative solution for incident preparedness.</p></li></ul><ul><li><p><strong>The Problem:</strong> Traditional tabletop exercises are often static, PowerPoint-driven, and lack engagement for modern technical leaders.</p></li><li><p><strong>The Solution:</strong> Reflex is an AI-driven platform that runs dynamic, OSINT-tailored tabletop simulations under realistic pressure.</p></li><li><p><strong>Behavioral Tracking:</strong> It detects human factors like panic, mistakes, and cognitive overload to generate fact-based reports rather than opinion-based assessments.</p></li><li><p><strong>Platform Flexibility:</strong> Reflex can run combined or separate tabletops for tech and executive teams, model different personality types, and deploy rapidly.</p></li><li><p><strong>Remote Integration:</strong> Natively supports Zoom, Google Meet, and Teams. It uses AI agents to co-facilitate and ask role-specific questions.</p></li><li><p><strong>Market Disruption:</strong> Highly cost-effective and scalable, Reflex allows for frequent, targeted tabletops rather than expensive, one-off traditional engagements.</p></li></ul><ul><li><p><strong>Target Audience:</strong> Ideal for large enterprises (like Cisco) and private equity firms needing high-quality, frequent tabletops across multiple portfolios on a budget.</p></li><li><p><strong>Security Training:</strong> Provides an immersive alternative to standard security awareness training by actively engaging users in common scenarios like MFA bypasses or USB risks.</p></li><li><p><strong>Future Vision:</strong> Enables organizations to track measurable team improvement over time, helping meet strict compliance and third-party preparedness expectations.</p></li></ul><ul><li><p><strong>Financial Status:</strong> Backed by professional VCs, Reflex emerged from stealth in January after a year of development. It is pre-Series A but has a secure, multi-year financial runway.</p></li></ul><p>Den and Cassio advise aspiring leaders to know their “why” and pursue disruptive strategies rather than the status quo. Reflex is highlighted as a low-friction, risk-reducing alternative for budget-constrained CISOs. The episode concludes by celebrating the partnership between 909 Cyber and Reflex, emphasizing a shared goal of revolutionizing organizational tabletop exercises.</p><p><br></p>