In today’s age of technological disruption, there’s no point in shying away from AI any longer. In fact, it’s detrimental to do so. In this episode of When Trust Meets AI, host and CEO of Drata, Adam Markowitz, welcomes Olivia Rose, a veteran CISO and virtual CISO advisor, to explore how AI is reshaping trust (both organizationally and personally), why GRC leaders need to embrace AI now or risk obsolescence, and how to reframe security as a driver of business value rather than a blocker. The truth is: the former GRC team no longer exists (or shouldn’t) and the security leaders winning today are the ones positioning themselves for tomorrow. So, tune in and flip through their playbook.

What You’ll Learn:

How AI is collapsing the boundary between personal and professional risk
Why your industry's tech debt determines your AI success more than your AI strategy
The framework for AI enablement before AI security
How GRC has transformed from a compliance checkbox into a revenue-protecting function
Why CISOs are burning out at scale and what actually supports them
The non-negotiable skill for surviving AI disruption in GRC
How to stop undermining yourself as a woman in tech

Olivia is a veteran cybersecurity executive and virtual CISO with over 24 years of industry experience, including two tenures as a Chief Information Security Officer. As the Founder of a successful executive advisory boutique, she brings deep expertise in AI enablement, trust architecture and the evolving intersection of personal and professional cybersecurity. Her insights on navigating tech debt, vendor risk assessment and the human elements of compliance make her an important voice for security leaders and GRC professionals seeking to position their teams as strategic enablers rather than operational blockers.

Episode resources:

Olivia Rose on LinkedIn: https://www.linkedin.com/in/oliviarosecybersecurity/
Rose CIO Group Website: https://www.rosecisogroup.com/
Adam Markowitz on LinkedIn: https://www.linkedin.com/in/markowitzadam
Drata Website: https://drata.com/

Highlights:

00:00 Introduction
01:03 From CISO to Virtual Advisor
02:15 How AI Is Blurring Personal and Professional Trust
05:18 AI’s Biggest Use Cases and Surprises
08:38 Tech Debt Is Your Real AI Bottleneck, Not Strategy
14:35 What It Means to Be a CISO Today
18:00 Why GRC Is Now a Revenue-Protecting Strategic Function
27:09 What Keeps CISOs Up at Night & Being an Unsung Hero
29:51 A Quote That Changed Olivia’s Life
32:39 The Power of Authentic Listening in Leadership
34:38 Women Leaders Need to Stop Self-Sabotaging
41:09 GRC Can’t Afford to Ignore AI Any Longer
43:05 Key Takeaways & Closing Thoughts

Quotes:

With this influx of AI, the lines between your personal and your professional life are very blurred now, and I've started to really emphasize the importance of trust on a personal level as well."
“AI doesn't pretty stuff up. It shines a big old flashlight on what you're doing wrong, and industries that have high levels of tech debt typically are gonna have the hardest time moving forward with AI."
"GRC people have it really tough, and it's underestimated how difficult it is to be a GRC person. But with the introduction of AI, you're having a lot of these tasks where you would be pestering and asking for evidence over and over again, or you don't even need to ask for it at all - it just automatically appears."
"Ten years ago, it was all spreadsheets with inaccuracies and manual updates. But the rate of efficiency and innovation we're about to see with AI is nothing compared to what we saw before. Within two to three years, the whole landscape is going to look completely different."