Last week, San Francisco's Fang Restaurant hosted something special. It was a gathering where the future of AI security wasn't just discussed, but actively shaped by the people building it. The Modern CISO Connect dinner, hosted by Caleb Sima and sponsored by Relyance AI, brought together an exclusive group of security leaders who are pioneering approaches to challenges that didn't exist in any playbook just two years ago.
For those unfamiliar with Caleb, he's become one of the most influential voices in the Bay Area CISO community and beyond. As a strategic advisor to Relyance AI and a veteran security leader who's built and scaled security programs across multiple high-growth companies, Caleb has earned a reputation for cutting through the noise to focus on what actually works.
The Room That Matters
This wasn't your typical vendor dinner. The guest list read like a who's who of security innovation: CISOs from Adobe, Zuora, and Verkada sat alongside security leaders from Anthropic, 1password, and Apple. Aptos Retail’s CIO shared insights with Cohesity's Head of AI Engineering, while the CISO from Tools for Humanity (the company behind Worldcoin) exchanged perspectives with security leaders from Credit Karma and Sierra.ai.
The diversity of industries represented (from fintech and retail to AI development and automotive) created a unique cross-pollination of ideas that you simply can't replicate in single-industry forums.
Beyond Presentations: Real Talk About Real Problems
What made this evening stand out was its format. No PowerPoints, no product pitches. Just Caleb moderating an interactive conversation where seasoned practitioners shared what's actually working (and what isn't) in securing AI-driven organizations.
The discussion was remarkably candid. Leaders openly discussed their failures, shared specific tactical approaches, and recommended emerging tools based on early deployment results. When the CISO of a major financial services company mentioned struggling with shadow AI discovery, three others immediately jumped in with their own solutions and vendor recommendations.
This kind of practical knowledge exchange (where multi-million dollar security decisions get shaped by peer insights rather than marketing materials) is exactly why invitation-only gatherings like this have become so valuable.
Four Key Takeaways That Define Today's Security Landscape
1. We're All Still Figuring This Out
The most honest takeaway from the evening? None of us has AI security completely figured out yet, and that's okay. The leaders in that room (some managing security for companies with billions in revenue) openly acknowledged they're building the plane while flying it. What matters isn't having all the answers; it's having the right framework for finding them quickly.
2. The Old Playbooks Don't Scale
Traditional data loss prevention and access controls weren't designed for environments where data flows through AI models, gets transformed, and emerges in completely new contexts. Several leaders shared examples of their existing tools generating thousands of false positives when applied to AI workloads, forcing them to either accept blindness or dedicate entire teams to manual triage.
3. Speed Beats Perfection in AI Security
The consensus was clear: organizations that wait for perfect AI security solutions will lose competitive advantage to those willing to implement "good enough" controls that evolve rapidly. One CISO put it perfectly: "We're not trying to build Fort Knox around our AI. We're trying to build smart guardrails that learn and adapt."
4. The Future Belongs to Integrated Approaches
The most interesting discussions centered around tools and platforms that blur traditional boundaries between privacy, security, and AI governance. Leaders consistently gravitated toward solutions that provide unified visibility rather than adding another dashboard to monitor. As one attendee noted, "My team doesn't have bandwidth for point solutions anymore. Everything needs to integrate or it doesn't get deployed."
The Conversations Continue
What happens at these dinners doesn't stay at these dinners—it shapes industry direction. The strategies discussed, the vendor recommendations shared, and the tactical approaches validated become the blueprint that other organizations follow. Several attendees mentioned they'd be reaching out to peers from the dinner to continue specific conversations, and at least two potential collaborations were born from chance encounters during the cocktail hour.
For those who joined us: the conversation continues. For those who didn't: we'll see you at the next one.
The Modern CISO Connect series brings together security leaders who are actively defining what comes next in our industry. Space is intentionally limited to practitioners pioneering new approaches to emerging challenges. Stay tuned for announcements about upcoming gatherings.
