In this insightful episode of Chasing Entropy, host Dave Lewis welcomes cybersecurity veteran Allison Miller to explore the intersections of fraud, risk, complexity, and AI in the ever-evolving digital landscape.

Allison brings two decades of experience spanning enterprise cybersecurity, anti-fraud, and advanced product risk. From traditional financial institutions to cloud-native startups, her work bridges how technology enables connection—and how those same systems can be exploited.

She shares her early fascination with communication networks, her journey through IRC, payphone hacks, and digital commerce, and how those formative experiences shaped her career.

Key Topics Covered

Chasing Risk and Complexity

Fraud as a window into system weaknesses — Allison explains why fraud fascinates her: it’s about understanding how things can go wrong even when the code is working as designed.
She discusses how payment systems, platform identity abuse, and communication channels become targets precisely where their value lies.

The Role of AI in Cybersecurity

AI as a detection tool: Building on her background in detection technologies, Allison sees AI as the next step in a lineage of data-driven defenses.
Three key AI applications:
→ Detection
→ Investigation assistance
→ Automation in Security Operations Centers (SOCs)
CISO responsibilities: While AI governance is still evolving, Allison highlights parallels with AppSec and suggests that product risk programs must incorporate AI security and safety.
Agentic AI and emerging risks: She warns that autonomous agents, while powerful, introduce new layers of system complexity that require holistic monitoring—simple components can combine into chaotic behaviors.

Future of Cybersecurity Leadership

Cloud, mobile, and multi-cloud continue to challenge traditional security models, requiring CISO teams to expand their skills and embrace innovation.
CISOs are now “chasing complexity” as much as they’re defending against it.

Advice for Aspiring Cybersecurity Professionals

Follow your curiosity rather than a linear career path.
Focus on interesting problems—your unique perspective will create opportunities.
Embrace networking and open conversations to accelerate learning and growth.

Quote of the Episode:
"Follow your curiosity. You can bring your interests into almost any job description—and that's where real opportunity lies." — Allison Miller

Tune in to this episode for a candid discussion that peels back the layers of how risk, fraud, and AI are shaping the cybersecurity front lines.

Subscribe to the Chasing Entropy Podcast for more real talk with the minds driving cybersecurity forward.

LinkedIn: Allison Miller, Founder & Principal, Cartomancy Labs

Website: Cartomancy Labs

Newsletter: Futurecast

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