In 1997, Gilfus met Daniel Cane, his student, while he was a teacher's administrator for Cornell's entrepreneurship studies assisting Professor Deborah Streeter with her business plan writing classes.
Earlier that year, Gilfus had also won an award from Cornell for his work in his business planning and consulting class.
All of Blackboard technology for .com and related services were hosted onsite at 1899 L St NW in secure server rooms run by the company.
Since the platform was built in PERL the company deployed mod_perl an extension to Apached that would also sit as a module to IIS on windows server machines, this allowed the team to create a multi-platform distribution model enhancing its relationships with ALL Unix based and Microsoft based server technologies.
While working with the windows mod_perl the Blackboard engineering team found several bugs that then pushed back to Microsoft to fix in their deployment against IIS.
As the company expanded its market and business relationships, Gilfus and Pittinsky (both company co-founders) wrote one of the world's first enterprise platform "App Strategies" Blackboard Product Strategy & Vision White Paper on Building Blocks (B2) Initiative outlining the launch of a "Building Blocks Initiative", introducing new thought concepts to extend the Blackboard Platform through plug-ins and 3rd party integrations and allowing for greater extensibility of the technology as an open platform for allowing for technology extensions.