Jim began his career in professional software development in 1987 by developing a series of widely distributed desktop applications for Houghton Mifflin Publishing Company.

In 1993, Jim co-founded Mathementors, later known as Innomatics, Inc., to advance development of revolutionary math tutorial software for Windows, Macintosh, and the web. His innovations have been ubiquitously adopted by the academic publishing industry for more than a decade.

Jim joined Boston-based Turning Point Software in 1995, where he managed product development projects for high-profile clients, including Hasbro Interactive, MicroTouch (now 3M), JIAN, Streamline.com, and Scholastic.

Jim extended his presence in the industry in 1998 when he founded Serenity Software, Inc., providing high-quality software development services to companies such as Motorola, Constellation NewEnergy, DCI Acquisition Corporation, and Inera, Inc.