DeJon Gaines
Most digital transformations fail because they're technology projects pretending to be business transformations. Real change happens when you reimagine how organizations create value—not just upgrade their infrastructure.
Leading technology transformation for 2,000+ enterprise clients across healthcare, financial services, and government. Orchestrating strategy for 65,000 employees with a focus on AI implementation, culture change, and sustainable competitive advantage.
I don't just advise on AI transformation—I'm building my own on-premises AI infrastructure (NVIDIA DGX) to understand the real economics, security trade-offs, and performance implications that enterprise leaders face.
📍 Lexington, Kentucky | 🎓 McKinsey Executive Leadership | 🎤 Keynote Speaker
What I'm Exploring Now
The questions keeping me up at night—and the conversations I'm having with enterprise leaders
The Hidden Economics of On-Premises AI
Everyone's rushing to cloud AI without doing the math. I'm setting up NVIDIA DGX infrastructure to answer the real questions: What's the actual cost per inference? Where's the break-even point vs. cloud? When does data sovereignty trump convenience? Running hands-on experiments to understand what enterprise deployment actually costs—not what vendors promise.
The Post-AI CIO Role
If AI handles execution, what's left for the CIO? I'm watching the role transform from "keeper of systems" to "architect of capability." But most organizations aren't ready—they're hiring for the old role while needing the new one. What does leadership actually look like when AI does the technical work?
Why Culture Still Eats AI Strategy
Every company can buy the same AI tools. But winners aren't determined by technology—they're determined by whether your culture can actually change how 25,000 people work daily. Technology is easy. Changing ingrained behaviors, incentive structures, and team dynamics? That's the real transformation challenge.
Building Transformation Muscles That Survive Leadership Turnover
Most transformations die when the champion leaves. I'm focused on a different question: How do you build organizational capabilities as muscle memory rather than one-time projects? What makes change stick when the next CIO arrives with their own agenda?
These aren't just abstract questions—they're the core of my speaking engagements, advisory work, and hands-on experimentation. If you're wrestling with any of these challenges, let's talk.
🧪 AI Lab
Where theory meets hardware. Building on-premises AI infrastructure to understand what enterprise leaders actually need.
Why Run Local AI Infrastructure?
Most executives talk about AI transformation while outsourcing everything to cloud providers. I'm taking a different approach: building hands-on experience with on-premises AI infrastructure to understand the real economics, security implications, and performance trade-offs that enterprise leaders face.
🔒 Data Sovereignty
Testing models without sending proprietary code or data to external APIs. Critical for regulated industries.
💰 Real Economics
Understanding the true cost per inference, break-even points, and when cloud vs. on-prem makes sense.
⚡ Performance Reality
Measuring actual latency, throughput, and reliability for enterprise-scale deployments.
Current Status: Setting up NVIDIA DGX infrastructure
Planning to run experiments on model fine-tuning, code generation, and enterprise AI deployment patterns. The goal isn't to build products—it's to understand what actually works at scale so I can advise organizations more effectively.
💡 Interested in the economics and architecture of on-premises AI? This is a major focus of my 2026 speaking and advisory work.
Operations at Scale
Testing deployment patterns at realistic operational volumes
Let's Engage
I'm interested in conversations about where enterprise technology is heading—not where it's been. Whether you're wrestling with transformation challenges, looking for a keynote speaker who won't bore your audience, or exploring advisory relationships, let's talk.
Speaking Engagements
Keynotes and workshops on AI transformation, strategic leadership, and the future of the CIO role. No generic advice—real stories, real results.
Strategic Advisory
Board advisory and consulting for organizations serious about transformation. I work with leaders who want to build capability, not just deploy technology.
Executive Conversations
Coffee chats (virtual or in-person) with fellow leaders navigating transformation. The best insights come from peer conversations, not consultants.
Email: dejon@digitalgaines.com
Based in Lexington, Kentucky