For the last 30 years, email security has been stuck in the past, focusing almost entirely on stopping bad things from getting into the inbox. In this episode, Rajan Kapoor, Field CISO at Material Security and former Director of Security at Dropbox, argues that this pre-breach mindset is dangerously outdated. The real challenge today is post-breach: protecting the sensitive data that already lives inside your mailboxes.

The conversation explores why we must evolve from "email security" to the broader concept of "workspace security" . Rajan explains how interconnected productivity suites like Google Workspace and Microsoft 365 have turned the inbox into a gateway to everything else Drive, accounts, and sensitive company data. We also discuss how the rise of AI co-pilots will create new risks, as they can instantly find and surface over-shared data that was previously hidden in plain sight .

Guest Socials - ⁠⁠Rajan's Linkedin⁠

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Questions asked:

(00:00) Introduction(02:00) Who is Rajan Kapoor? Field CISO at Material Security(02:38) What is Email Security in 2025? The 30-Year-Old Problem(03:20) The Critical Shift: From Pre-Breach to Post-Breach Protection(04:20) The Rise of Workspace Security: Beyond the Inbox(06:00) Why Focusing on Email is "Not Even Half" The Problem(06:50) Are Microsoft 365 Security Challenges Different from Google's?(09:30) Rethinking the Approach to Email Security(11:40) How AI Co-Pilots Will Exploit Your Over-Shared Data(13:30) A Real-World Attack: From Email to Malicious OAuth App(17:00) How Should CISOs Structure Their Teams for Workspace Security?(19:25) The Role of CASB vs. API-Based Security for Data at Rest(23:10) How CISOs Can Separate Signal From Noise in a Crowded Market(24:45) Final Questions: Home Automation, Career Risks, and Ethiopian Food