If your AI solution is just helping humans process the same amount of alerts a little faster, you haven't transformed anything, you've just created a faster hamster wheel.In this episode, Ashish and Caleb speak with Heather Ceylan, CISO at Box.com, about how she is leading a true, developer-first AI transformation within her security organization . Heather reveals the five strategic "AI Bets" Box is making. We dive into the reality of building an AI SOC, discussing how Box achieved a 38% automated triage rate for Tier 1 alerts, and why teaching AI not to hallucinate requires treating prompts like strict policy engines .The conversation also tackles the build vs. buy dilemma. Heather explains why she prefers to have her team build custom AI solutions (at least until vendors can out-innovate her engineers) and shares her biggest disappointment when evaluating AI security startups

Questions asked:

(00:00) Introduction(02:50) Who is Heather Ceylan? (CISO at Box.com) (04:20) Transformation vs. Acceleration: Eliminating Classes of Work (06:00) Building an AI SOC: Achieving 38% Automated Triage (07:20) Controlling Hallucinations: Prompts as Policy Engines (09:30) The Buy vs. Build Debate for CISOs (14:00) Why Security Architecture Must Be Machine Consumable (16:50) The Problem with 3rd Party Risk Management (18:20) Box's "5 AI Bets" Framework (21:30) Will AI Replace SOC Analysts? Why Teams Are Embracing the Change (23:50) Continuous Pen Testing & Evaluating AI Startups (26:30) The Biggest Pitching Mistake Startups Make with CISOs (30:20) Shadow AI: When the Business Starts Building Its Own Apps (37:30) Personalized Software: The LEGO Brick Model of Security Agents (41:50) Fun Questions: Crocodile Jerky and Tim Tam Slams (44:20) Hobbies & Family: Raising Two Boys and Surviving the Chaos (45:30) Favorite Restaurant: Meyhouse (Turkish Cuisine in Palo Alto)

Resources discussed during the episode:

• Heather's LinkedIn Newsletter
• Heather's post RSA blog
• 5 Big AI Bets

1. https://blog.box.com/big-cybersecurity-bets-part1
2. https://blog.box.com/big-cybersecurity-bets-part-2
3. https://blog.box.com/big-security-bet-3-ai-redefines-vulnerability-management
4. https://blog.box.com/5-big-cybersecurity-bets-4-scaling-security-architecture-ai-first-world
5. https://blog.box.com/5-big-cybersecurity-bets-continuous-adversarial-validation