Fractional CIO leadership for companies tired of paying for bad IT decisions.
Rare Leadership. Real Results.
Led by Ryan Drumheller. Executive technology leadership without the full-time CIO cost. Clarity, momentum, and the operating discipline most mid-market companies are missing.
Free 30-minute call. No sales pitch.
Ryan Drumheller
Executive IT Leader • Fractional CIO • Advisor
Executive Support
For companies that need direction more than another tool.
Most of the businesses I talk to don't need more technology noise. They need someone who can sit at the leadership table, set priorities, and connect what IT, cybersecurity, modernization, and AI actually mean for the business.
What is a Fractional CIO?
The CIO seat, without putting a CIO on the payroll
A fractional CIO is a senior technology executive who operates inside your leadership team without taking a permanent seat on the payroll. You get the same caliber of strategic judgment and operational experience you'd get from a C-level hire, without paying for an executive search, a full salary, or a long-term commitment you can't unwind.
Most mid-market companies don't need a CIO permanently on the org chart. What they need is senior technology leadership in the room when it actually matters, with the flexibility to shape that engagement as the business changes. That's the gap I fill.
Why companies bring me in
What you actually get when we work together
You're not buying hours. You're getting a leader who takes ownership of the technology decisions slowing your business down, and who sticks with you long enough to fix them.
A CIO seat for a fraction of the cost
You get senior technology leadership for a fraction of what a full-time CIO would cost. No salary, equity, or benefits load to carry.
Engaged in days, not months
A typical CIO search takes six to nine months. I'm usually productive inside the first two weeks.
Sized to where you are
Scale me up during a transformation, dial me back once things settle. The engagement flexes with the business so you're never paying for support you don't need.
Patterns from dozens of companies
Over twenty years I've seen what works and what quietly falls apart. You get the benefit of those patterns instead of one person's narrow career path.
Honest perspective, not politics
I don't have a seat to protect or a team to grow. That means I can tell you what's actually working, what isn't, and where the next risk is hiding.
Strategy and the execution to back it up
You get a board-ready point of view, plus the willingness to roll up my sleeves and help your team actually deliver on it. Both, from the same person.
AI Leadership
Making AI actually move the business forward
Most of the companies I talk to are already playing with AI in some form. The problem isn't curiosity. It's that the experiments have no owner, no guardrails, and no connection to the business outcomes the leadership team actually cares about. When AI sits in that gap, it usually adds risk faster than it adds value.
I help leaders build an AI plan that fits the business they already have. That means picking the use cases worth chasing, putting governance and security in place before things scale, and making sure AI shows up in the systems your people already work in.
An AI roadmap built around the business, not the latest tool
Governance, risk, and acceptable-use guardrails leadership can sign off on
Vendor and platform selection without the hype
Integration with the systems your team already uses
Security, privacy, and data protection across AI workflows
Executive alignment on what AI changes and what it doesn't
Who I work with
Companies in the moments where technology decisions matter most
Growing companies
You need an executive technology voice in the room. You're just not ready to carry the cost of a full-time CIO yet.
Private equity and M&A teams
You need a steady set of eyes on IT diligence, integration plans, and the technology risks that show up in every deal.
Mid-market businesses
Your IT team is solid, but the strategy and governance layer above them is missing. That's the seat I fill.
Companies under pressure
Something broke, someone left, or the board is suddenly paying attention. You need a calm operator who can stabilize the room and lead a plan.
How we work together
Three ways to bring me in, sized to where you are.
Some companies want me embedded as their fractional CIO every week. Others want me as a sounding board for the harder calls, or focused on a single project that has to land. The standard of judgment is the same in all three.
Fractional CIO
I take the CIO seat on your leadership team without the full-time price tag. Strategy, governance, vendor decisions, security posture, and AI direction, all owned by one person.
Advisory
An executive sounding board for the technology, AI, security, and modernization calls your leadership team is wrestling with.
Projects
Leadership on the technology initiatives that have to land. ERP, cyber response, cloud migration, M&A integration, anything where the stakes are too high to learn on the job.
What people actually say
Reviews from podcast guests, podcast hosts, and former colleagues across more than two decades of IT leadership. Pulled directly from PodMatch and LinkedIn.
I had a lovely experience as a guest on Decline Invite. Ryan is a great host, clearly passionate about the work he's doing through his pod. He came well prepared and facilitated the convo in a way that felt natural. I'm certain it will be an engaging pod episode. I'd recommend the pod, and would absolutely record with Ryan again.
Kurt Bush
Decline Invite guest
20 May 2026
Best preparation by a Host I've seen in 135 shows I've done.
Roy Osing
Decline Invite guest
18 May 2026
Ryan did a fantastic job. He has a calm conversational way of delivering technical information. So many golden nuggets from the conversation. Highly recommend.
Stay Hungry Podcast
Podcast host
14 May 2026
Ryan brings a grounded, no fluff perspective to leadership in a tech driven world shaped by 20+ years navigating complex environments from cybersecurity to large scale transformations. What stood out was his focus on cutting through complexity, helping leaders make decisions that actually move things forward, not just sound impressive. Ryan shows up with directness and real world clarity, making the conversation both honest and immediately useful.
BizBlend
Podcast host
01 May 2026
I had the pleasure of managing Ryan Drumheller during his time as IT Manager at NeoPollard, where he led a team of technicians while overseeing both our internal IT operations and client support. Ryan brought real leadership to the role. He is calm under pressure, solutions oriented, and someone his team genuinely rallied around. He balanced a demanding dual workload with professionalism and consistency, and he advocated equally well for his people and the business. His technical skills were never in question, but it's his ability to lead, communicate, and build trust across the organization that truly set him apart. Any company would be lucky to have him.
Jay Whitmore
Director of Information Security at KERV.ai
Jay managed Ryan directly
14 May 2026
I had the pleasure of working with Ryan Drumheller as my manager, and now call him a friend. He's one of the most driven and supportive leaders I've ever worked with. He's big on continuous learning and growth, not just for himself, but for everyone around him. His ability to connect technology with business strategy is impressive, and he leads with a people first mindset that makes a real impact. Anyone would be lucky to work with or learn from him.
Colin Courter
Systems Engineer
Colin reported to Ryan directly
3 June 2025
Ryan has that energy that brings people together and working for this individual has been a blessing. Ryan really cares about his team, organization, and is always willing to go that extra mile to make sure everyone is happy and has all the resources to succeed. Out of all the great things this individual has going for him, one that stands out the most to me is his willingness to mentor you on how to be successful in your IT career. I personally wouldn't be where I am today if it wasn't for him taking a chance on me. He is one of those leaders that will get in the trenches with you when things are not going right and walk out of them with you when the situation has been resolved.
Dustin Smith
System Engineer at NeoPollard Interactive
Dustin reported to Ryan directly
5 October 2023
About Ryan
Twenty-plus years leading IT inside real companies. Big enterprises, mid-market businesses, M&A integrations, cybersecurity programs, and modernization work that actually shipped. That's the experience you're getting when you bring me in.
20+ years leading IT inside real companies
Comfortable in front of executives and boards
Hands-on M&A and cybersecurity background
People come first, technology second
Want to talk?
Whether you're looking for an embedded fractional CIO, an advisor for the harder calls, or leadership on a project that has to land, the first step is the same. A 30-minute call to figure out if I'm the right fit.