Governing Body Spotlight

Bruce Phillips is an award-winning cybersecurity executive and current Chief Information Security Officer for a national title and escrow company. With more than 25 years of experience spanning defense, financial services, and real estate technology, he has been recognized as one of the Top 100 Information Security Professionals by OnCon in 2025. Bruce also leads Cyber411.ai, a thought leadership platform dedicated to helping real estate and financial professionals strengthen their cybersecurity posture.

Fun fact: Before his cybersecurity career, Bruce served aboard U.S. Navy submarines maintaining strategic navigation systems—a role that taught him precision, discipline, and the importance of teamwork under pressure.

Learn more about the Chicago CISO community here.
 

Give us a brief overview of the path that led to your current role.

My path to becoming a CISO began in the United States Navy, where I served as a submariner responsible for operating and maintaining strategic navigation systems. That experience instilled in me the rigor and attention to detail that still guide my approach to cybersecurity today. After leaving the Navy, I continued my work in the defense industry supporting submarine weapon systems before transitioning into application development and engineering—where I helped shape some of the early principles of application security. Over time, this blend of technical expertise and mission focus naturally evolved into leadership roles in risk management and cybersecurity.
 

What is one of your guiding leadership principles?

Lead with clarity and empathy. Security isn’t just about controls—it’s about people. My role is to make security understandable, practical, and achievable across the organization, creating a culture where everyone shares responsibility for protecting our clients and our company.
 

What is the greatest challenge CISOs face today, and how are you addressing it?

The greatest challenge today is managing risk in an AI-driven, highly interconnected ecosystem. Emerging technologies are transforming how business operates, but they’re also creating new threat vectors and compliance challenges. I’m addressing this by embedding AI governance and data protection into our broader enterprise risk strategy—focusing on enablement and accountability rather than restriction—so innovation and security move forward together.
 

What is the key to success for someone just starting out as a CISO?

Listen first and learn the business. You can’t secure what you don’t understand. Build relationships early, communicate in business language, and focus on enabling outcomes rather than enforcing controls. The most effective CISOs are those who earn trust through collaboration and consistency, not through fear or technical complexity.
 

How do you measure success as a leader?

Success is measured by resilience and trust. If the organization can withstand disruption, continue operating, and maintain stakeholder confidence, that’s a strong indicator of leadership impact. I also measure success by how well my team grows—when they take ownership, solve problems independently, and elevate the program, that’s the clearest reflection of leadership done right.
 

What is the value of being a member of Gartner C-level Communities?

Gartner C-level Communities offers a rare opportunity to exchange ideas with peers facing similar challenges. The collaboration and candor within this community help sharpen our collective approach to leadership, risk, and resilience—reminding us that while our industries differ, our mission to protect trust remains the same.
 

Gartner C-level Communities Governing Body members share their insights and leadership perspectives to shape the agendas and topics that address the top priorities impacting business leaders today.