Randy Dougherty is the Chief Information Officer (CIO) at Trellix, a global cybersecurity company. His 25-plus year career journey is rooted in an early passion for technology and includes key leadership roles at Wellcare, The Nielsen Company, and eXp Realty. He is an experienced leader in large-scale infrastructure and digital transformation, having navigated the evolution from mainframe data centers to cloud environments and successfully steered multiple large-scale double carve-out exercises. As CIO, he drives the enterprise technology and operations strategy, emphasizing cost optimization and embracing cross-functional alignment between IT, security, and the business. He is a strong proponent of using AI as a lever for workforce augmentation and is focused on tackling the immense challenge of data management. Recently, in an exclusive interview with CIO Magazine, Randy shared insights into his career journey, emphasizing his unexpected transition from premed studies to a passion for technology and leadership roles at prominent organizations. He also discussed the challenges facing technology leaders, the intersection of technology and business, and his approach to staying ahead of the curve. The following excerpts are taken from the interview.

Hi Randy. Can you walk me through your career path and how you got to where you are today?

It's a journey that started in a really unexpected place: I was a premed student at the University of Miami, ready for a career in medicine, when I found this compelling, irresistible passion for computers and programming. That early interest—that shift in focus—set the course for everything. Instead of going to medical school as I originally planned, I ended up earning my MBA in Information Technology, and I never looked back. I made the transition from that early passion into core technology leadership, gathering key experiences at organizations like Wellcare, Nielsen, and eXp Realty before joining Trellix. My time at Nielsen was a masterclass in scale, where I led a massive matrixed team of global associates. And at eXp Realty, I had to move incredibly fast: we scaled Global IT Operations to support over hundreds of thousands of agents across the globe in record time, driving a significant increase in public share value. I've literally seen the evolution of IT, from working in mainframe data centers to navigating today's complex cloud and metaverse environments. Along the way, a few core lessons have become my guiding principles: a relentless focus on cost optimization—which has allowed me to eliminate over a substantial amount in annual expense at Trellix —the deep belief that security is everyone's responsibility, and the idea that, within an agile framework, failure is simply a valuable learning opportunity. This broad, hands-on experience ultimately prepared me to lead the Enterprise Technology and Operations strategy here at Trellix.

What aspects of your role as a CIO do you find most rewarding, and why?

What genuinely energizes me is the opportunity to be a true partner to the business and drive measurable, tangible improvements. I don't see my job as sitting in an IT silo. I spend a significant amount of time collaborating with leaders across the organization—in sales, customer success, and finance—to truly understand their critical business drivers, things like ARR and the imperative of cost reduction. The deep satisfaction comes from effectively translating those business needs into technological solutions that don't just keep the lights on, but actually fuel sales, improve customer success, and measurably reduce costs and enhance efficiency. For instance, a standout moment at Trellix was leading the consolidation of 10 global data centers in one year, which eliminated over a significant amount of annual operating expense with minimal operational interruption. That's the core mission: ensuring every technology investment has a clear business case and drives a powerful return.

What do you believe are the most significant challenges facing technology leaders today, and how do you stay ahead of the curve?

The most significant operational challenge, in my opinion, is managing the sheer volume and velocity of data we're dealing with today. At the same time, we CIOs are under immense pressure to manage growing technology costs while constantly needing to integrate major innovations like Artificial Intelligence. To stay ahead, I focus on continuous simplification and discipline. I prioritize investments that hit core business objectives while simultaneously improving our security and resilience. My approach is to simplify priorities, maintain a critical sense of urgency, and consciously avoid being sidetracked by the next "shiny thing.” I know from experience that you need a healthy, optimized underlying foundation before you pour money into any new technology. This discipline is key to maintaining focus and unity across all teams.

How do you think about the intersection of technology and business, and what role do you see technology playing in driving business outcomes?

My perspective is firm: Technology isn't a silo; it has to be completely integrated into the business strategy. As CIO, my primary role is to be a key partner to the business, ensuring our tech initiatives align directly with major company goals. Technology is the essential lever for achieving business outcomes. It provides the necessary tools to fuel sales, enables better customer success outcomes, and measurably reduces costs and enhances operational efficiency. Every investment must solve a problem and demonstrate a clear return. I view AI not as a silver bullet, but as one lever for workforce augmentation and optimization that achieves true value when used in concert with parallel process improvements.

Can you share a mentor or role model who has had a significant impact on your career, and what advice they gave you?

One of the most impactful mentors in my career was someone who truly embodied resilience. He faced incredible health challenges, battling cancer and enduring a stroke, yet he never let that stop him. He was a dedicated marathon runner, and he used his own journey as an example, showing me how he continued to run marathons despite everything. His unwavering spirit and determination were incredibly inspiring, and it was through his encouragement and example that I was motivated to run my first marathon. He taught me that no matter the obstacles, with perseverance, you can achieve your goals and push beyond your perceived limits.

What are some of your passions outside of work? What do you like to do in your time off?

I'm a dedicated runner with over ten marathons completed. Running is my way of practicing discipline, endurance, and pushing limits—it provides a great counterbalance to the demands of my professional life. I also stay committed to community service as a local mentor and advocate, and my family and I love to travel and explore global food and wine cultures.

Can you share a book, podcast, or resource that inspires you, and why?

Ray Dalio's "Principles" has profoundly inspired me as a CIO. His emphasis on radical truth and radical transparency, coupled with a systematic approach to decision-making, resonates deeply with my role. Dalio's framework for understanding and learning from mistakes, viewing them as valuable data points for improvement, aligns perfectly with the agile mindset I champion. It reinforces the idea that within an agile framework, failure is simply a valuable learning opportunity, which is essential for any technology leader driving modern transformation. This philosophy encourages calculated risk-taking and relentless improvement, both critical for navigating the complexities of today's technology landscape.

What is your favorite quote?

It's a quote that speaks directly to the mindset of a technology leader driving change: “If you’re not failing, you’re not pushing your limits, and if you’re not pushing your limits, you’re not maximizing your potential.” — Ray Dalio. This quote resonates deeply with me because I’ve been guided by the core lesson that within an agile framework, failure should be viewed as a valuable learning opportunity. It’s a belief that encourages calculated risk-taking and relentless improvement—which is essential for any technology leader driving modern transformation.

What is your biggest goal? Where do you see yourself in 5 years from now?

My biggest goal, day-to-day, is to maintain a healthy, resilient, and optimized technology foundation at Trellix that directly translates into business advantage. In the next five years, I anticipate continuing to lead significant digital transformations, building on the current wave of AI to explore the next evolution, which I believe may even involve robotics and the physical manifestation of AI. I see myself continuing to guide the organization through the inevitable transition from the current rapid AI adoption phase into a balanced, settled hybrid environment, ensuring Trellix remains a technological and security leader.

What advice would you give to aspiring CIOs or technology leaders looking to make a similar career journey?

I have four pieces of advice that I live by:

1. Be a Partner, Not a Provider: Understand that your role is a partnership with the entire business. You must learn to effectively translate the needs of executives in sales, finance, and customer success into tangible technological solutions.
2. Make Security Your Co-Pilot: Embrace security as a core partner, not a barrier, and integrate it into development from the ground up, following a DevSecOps mindset.
3. Demand a Business Case for Everything: Be disciplined in your investments. Always demand a clear business case that demonstrates the technology will tangibly fuel sales, reduce costs, or improve efficiency.
4. Build a Strong Foundation First: Finally, remember that AI and other new technologies are only effective if you have a strong, scalable foundation beneath them. Don't pour money into new innovations without first optimizing your underlying processes.