AI CTF: gamified security training

Transitioning a mature organization from an API-first model to an AI-first model is no small feat. In this episode, Yash Kosaraju, CISO of Sendbird, shares the story of how they pivoted from a traditional chat API platform to an AI agent platform and how security had to evolve to keep up.

Yash spoke about the industry's obsession with "Zero Trust," arguing instead for a practical "Multi-Layer Trust" approach that assumes controls will fail . We dive deep into the specific architecture of securing AI agents, including the concept of a "Trust OS," dealing with new incident response definitions (is a wrong AI answer an incident?), and the critical need to secure the bridge between AI agents and customer environments .

This episode is packed with actionable advice for AppSec engineers feeling overwhelmed by the speed of AI. Yash shares how his team embeds security engineers into sprint teams for real-time feedback, the importance of "AI CTFs" for security awareness, and why enabling employees with enterprise-grade AI tools is better than blocking them entirely .

Questions asked:

Guest Socials - Yash's Linkedin

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If you are interested in AI Cybersecurity, you can check out our sister podcast -⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AI Security Podcast⁠

Questions asked:

(00:00) Introduction(02:20) Who is Yash Kosaraju? (CISO at Sendbird)(03:30) Sendbird's Pivot: From Chat API to AI Agent Platform(05:00) Balancing Speed and Security in an AI Transition(06:50) Embedding Security Engineers into AI Sprint Teams(08:20) Threats in the AI Agent World (Data & Vendor Risks)(10:50) Blind Spots: "It's Microsoft, so it must be secure"(12:00) Securing AI Agents vs. AI-Embedded Applications(13:15) The Risk of Agents Making Changes in Customer Environments(14:30) Multi-Layer Trust vs. Zero Trust (Marketing vs. Reality) (17:30) Practical Multi-Layer Security: Device, Browser, Identity, MFA(18:25) What is "Trust OS"? A Foundation for Responsible AI(20:45) Balancing Agent Security vs. Endpoint Security(24:15) AI Incident Response: When an AI Gives a Wrong Answer(29:20) Security for Platform Engineers: Enabling vs. Blocking(30:45) Providing Enterprise AI Tools (Gemini, ChatGPT, Cursor) to Employees(32:45) Building a "Security as Enabler" Culture(36:15) What Questions to Ask AI Vendors (Paying with Data?)(39:20) Personal Use of Corporate AI Accounts(43:30) Using AI to Learn AI (Gemini Conversations)(45:00) The Stress on AppSec Engineers: "I Don't Know What I'm Doing"(48:20) The AI CTF: Gamifying Security Training(50:10) Fun Questions: Outdoors, Team Building, and Indian/Korean Food