In this episode of The Segment, host Raghu Nandakumara sits down with one of the most influential technology leaders of our time: Tony Scott, President & CEO of Intrusion and former U.S. Federal CIO under President Obama. With CIO roles at Microsoft, VMware, Disney, General Motors, Bristol Myers Squibb, and Sun Microsystems, Tony brings a rare, decades-wide perspective on how enterprise technology evolves—and where it’s heading next.

Tony shares his journey through some of the world’s most complex organizations, offering a candid look at the forces that drive digital transformation, why organizational silos still shape most architectures, and how AI may finally help dissolve them. He breaks down how cybersecurity models must shift in an era of ubiquitous AI, legacy infrastructure, and escalating regulatory complexity—and explains why continuous monitoring and long-term institutional memory are now essential.

We also dive into Tony’s leadership philosophy, how he balances transformation with cyber risk, and what he’s learned transitioning from CIO to CEO of a cybersecurity company tackling some of today’s hardest problems.

Key themes discussed:

The evolution of the CIO role across decades of transformation
Managing cyber risk amid AI proliferation, legacy systems, and modern architectures
The importance of “useful life” frameworks for tech modernization
Leadership lessons from navigating both public and private sector tech at scale

A must-listen for CIOs, CISOs, tech leaders, and anyone preparing their organization for what’s next in AI-driven transformation and cybersecurity.

From the White House to the Boardroom: Tony Scott on Leading Transformative Tech