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Problem Solving Through Technology for Over 40 Years!

In a world where digital transformation is a necessity, Oakwood is the Microsoft Solutions Partner that brings clarity, innovation, and measurable results to your IT initiatives.

Why Oakwood?

Our People

At Oakwood, you’re not just working with consultants—you’re partnering with a team of experienced technologists, strategists, and problem-solvers dedicated to your success. Our people bring deep expertise, a collaborative mindset, and a commitment to delivering results that matter. We thrive on building long-term relationships, ensuring that every engagement is a step toward your transformation.

Our Process

Technology is complex, but working with Oakwood isn’t. Our proven Identify, Build, Design, Deploy methodology streamlines every engagement—from discovery to execution. We focus on practical, results-driven solutions, guiding you through every stage with transparency, agility, and a bias for action. No wasted time, no endless consulting cycles—just real outcomes.

Our Technology

As a Microsoft Solutions Partner, we specialize in unlocking the full power of Azure, AI, Data & Analytics, Security, and Modern Work. Whether you’re migrating to the cloud, modernizing applications, or leveraging AI, Oakwood brings the right tools, strategies, and innovations to accelerate your business. Our expertise ensures that technology works for you—not the other way around.

We Put People First

Clients

Our purpose is to serve the evolving needs of our clients in truly remarkable ways—always prioritizing their success above all else. We challenge conventional thinking, pushing beyond traditional benchmarks and redefining industry standards.

Company

We are a group of individuals connected by one goal; to serve others well. In life and at work, we embrace our differences and encourage collaboration. While one person can make a difference, we believe we are stronger when we work together.

Consultants

“Our mission is to empower our Consultants by removing traditional obstacles to career growth. We cultivate an environment where innovation, ambition, and expertise thrive, providing the resources, mentorship, and opportunities needed for success.

Community

There is another group of people we’re obliged to serve that goes far beyond the workplace. We believe there is a social responsibility to serve our community and those in need. We shouldn’t be here just to consume. We need to give of our time, talent and treasure.

Oakwood Leadership

Charles WindsorCEO
jeff reddin
Jeff ReddinVP Sales
Tonja HiltonVP Finance & Administration
michael caylor
Michael CaylorSr. Director of Cloud & Infrastructure
steve goodman - director of managed services
Steve GoodmanSr. Director of Managed Services
john trease
John TreaseDirector of Application Modernization
justin hunter
Justin HunterDirector of Data & Analytics
jason missildine
Jason MissildineSr. Director of Artificial Intelligence (AI)
tim haaksma
Tim HaaksmaDirector of Marketing