Trusted Technology Solutions for 40+ Years

Oakwood brings deep expertise, and a collaborative mindset and a relentless focus on delivering real business value.

ABOUT US

Oakwood brings deep expertise, and a collaborative mindset

Founded in 1981, Oakwood provides expert counsel and comprehensive solutions in the areas of modern work, application innovation, data & AI, cloud, and managed services.

Our People

Our team combines deep technical expertise with a collaborative culture focused on understanding your business and delivering outcomes that matter.

Our Process

We follow a proven methodology that balances agility with discipline, ensuring transparency, accountability, and continuous alignment with your goals.

Our Technology

We leverage leading platforms and modern architectures to build solutions that scale, integrate, and evolve with your organization.

Our Clients

OUR TEAM

Leadership that turns vision into action and strategy into results.

Evolving regulations, rising customer expectations, and aging systems make it difficult for financial institutions to innovate and operate efficiently.

Charles Windsor

CEO

Jeff Reddin

VP, Sales

Tonja Hilton

VP Finance, Administration

Michael Caylor

Sr. Director, Cloud & Managed Services

Steve Goodman

Sr. Director, of Managed Services

John Trease

Director of App Innovation & AI

Tim Haaksma

Director of Marketing

Charles Windsor

CEO

Jeff Reddin

VP, Sales

Tonja Hilton

VP Finance, Administration

Michael Caylor

Sr. Director, Cloud & Managed Services

Steve Goodman

Sr. Director, of Managed Services

John Trease

Director of App Innovation & AI

Tim Haaksma

Director of Marketing

Our Mission & Values

Deliver technology solutions with integrity, collaboration, and a relentless focus on real business outcomes.

Oakwood’s mission is to help organizations realize what’s possible with the Microsoft Cloud and turn vision into reality. We believe technology should simplify, not complicate, and that real progress comes from trusted, transparent partnerships. Guided by integrity, curiosity, and ownership, our team delivers thoughtful, well-crafted solutions with pride. Transformation is a shared journey and we remain accountable, committed, and focused on creating lasting impact.

OUR APPROACH

How we work at Oakwood

Our approach is built on transparency, collaboration, and a commitment to long-term partnerships. We align our processes with your goals and adapt as your needs evolve.