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

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