While studying microbiology and computer science in college, Thomas often tutored other students. That experience fostered his fascination with problem-based learning (PBL) as a superior mode of teaching to rote memorization.
After beginning his programming career at Virtual Communities, Thomas joined About.com as a senior programmer to develop online back-office software. Over the next two years, Thomas and his team created a proprietary software system called Sales Order System (SOS) as well as a cost-effective and fast method of organic software development.
While at About.com, Thomas was instrumental in developing a reporting platform for Sprinks, an ad-word advertising company purchased by About.com, as well as further expanding the capabilities of SOS. These custom software solutions attracted the attention of Google, AOL, and The New York Times-Google purchased Sprinks in 2003 and, after a bidding war, The New York Times purchased About.com in 2005, reportedly to gain access to SOS.
While implementing SOS for NYTimes.com and Boston.com, online divisions of The New York Times, Thomas revived his earlier interests in using technology to enable learning. In 2008, AIS Solutions recruited Thomas to join as the CTO of the company and Senior Project Manager for the Akeso project.