About
Ryan Drumheller
Fractional CIO • Technology Leader • Advisor • The Extroverted IT Leader
Rare Leadership. Real Results.
Technology Leadership Without the Full-Time CIO Cost
I help organizations bring structure, clarity, and leadership to their technology decisions. After more than 20 years in IT leadership, I have seen where businesses lose time, money, and momentum and what it takes to turn technology into a real business advantage.
My approach is practical, executive focused, and built for leaders who need stronger direction across technology, risk, operations, and change.
Credentials Snapshot
My Story
Built at the intersection of technology, leadership, and business execution
My career has been built at the intersection of technology, leadership, and business execution. I have led infrastructure, cybersecurity, cloud, operations, M&A, and transformation work while helping organizations make better decisions and move forward with more confidence.
What I saw over and over again was this: many organizations either had IT in place but no real executive direction, or were growing so fast that their technology foundation could not keep up. Both create the same problem — reactive decisions, increased risk, and slower execution.
Stellar Horn Group was built to solve that problem. It is a way for me to bring executive level leadership, strategic clarity, and practical guidance to organizations that need more than tactical IT support.
What I Bring
Executive technology strategy and prioritization
Leadership through complexity, risk, and growth
Business alignment for IT, cybersecurity, and operations
Clear communication with executives, boards, and teams
Mentorship and development for emerging leaders
Experience Highlights
A leadership path built on results, credibility, and a people first approach
Technology Leadership
Led major initiatives across infrastructure, cloud, cybersecurity, operations, and enterprise transformation.
M&A and Integration
Led major M&A integration efforts while balancing speed, security, continuity, and execution.
Cybersecurity and Risk
Helped leadership teams better understand risk and strengthen governance.
People and Mentorship
Built teams, developed leaders, and mentored future talent.
Selected Achievements
Results, leadership, and business impact
Helped drive major cost savings through smarter IT strategy and vendor decisions
Led large scale technology and cybersecurity initiatives across complex environments
Supported M&A integration efforts requiring speed, structure, and business continuity
Built and developed strong teams while mentoring future leaders
Created clarity for executives navigating technology risk, growth, and change
Why clients work with me
Clients are not just hiring someone with technical experience. They are hiring judgment, communication, leadership, and the ability to connect technology to real business priorities.
I bring an approach that is direct, practical, people first, and built for organizations that need stronger direction without unnecessary complexity.
Education & Credentials
Depth built through experience, study, and discipline
I take leadership and learning seriously. My education and certifications reflect that commitment.
MBA in IT Management
MS in Management and Leadership
Bachelor’s in Computer Science
Harvard Business School Certificate of Specialization in Leadership and Management
170+ certifications across leadership, governance, security, and technology
Selected credentials
Replace the placeholder links below with your direct certification URLs, Credly links, LinkedIn licenses, or credential detail pages.
Leadership and Management
Cybersecurity and Risk
Architecture, Governance, and Delivery
Cloud, AI, and Platforms
Why it matters
Credentials do not replace experience, but they do reflect discipline, curiosity, and a commitment to bringing real depth into the room.
Clients are hiring leadership, judgment, and the ability to connect technology to real business outcomes.
Ready to Connect?
Looking for executive level technology leadership?
If your organization needs stronger direction, better alignment, and a clearer path forward for technology, let's start the conversation.