In 1995, the principal owners of Fieldware, LLC started a company called On-Course Technologies, Inc. with the goal of developing their own technology products. Client consulting was used over the years to fund new product development and to expand the Company's software expertise. As the client consulting side of the business grew, it became apparent that it was a sustainable entity on its own. In 2000, the consulting business split from On-Course and started doing business as Fieldware, LLC. The two companies have the same majority ownership and share common office space in downtown Chicago.

Fieldware has been actively involved in corrections since the award of its first OffenderLink™ contract in 2002. Over the next few years Fieldware transitioned its focus from software consulting to OffenderLink™ exclusively. At this time 100% of the company's resources are dedicated to the support, enhancement and expansion of OffenderLink™.