Oakwood was founded with the mission of providing services on a new minicomputer IBM had developed, the System 38. Several years later, when the market began to shift to the IBM AS/400, Oakwood leveraged their relationship with IBM and became a dominant local firm utilizing the new technology. In 1989, the AS/400 was introduced and Oakwood was well positioned to be on the forefront of business with it.
As the maturity of the client/server technology began to advance, Oakwood recognized the need to expand their relationships to include some of the premier software providers including Microsoft. In 1994 Oakwood began developing its solutions on the Microsoft platform. Soon afterward, Oakwood became one of the first Microsoft partners in the Midwest region. In 2001, Oakwood became a Microsoft Gold Certified Partner, which was achieved through providing challenging technology solutions to many clients in the e-business, infrastructure and security specializations.
Since 1981, Oakwood has received numerous business distinctions and industry awards. Among them is being placed on St. Louis’s Fastest 50 Growing Technology Firms list for five consecutive years. Microsoft has recognized Oakwood on several occasions, notably including Central Region’s “Partner of the Year” for Competency for 2005, "Partner of the Year" for Marketing Excellence in 2006, and as a "Partner of the Year" finalist for Competency in 2007. The Saint Louis Business Journal named Oakwood as one of the fifty fastest-growing privately held firms in 2007, and as one of the Midwest's top consulting firms in 2008.