Kyle's innovative work in education is a career that spans nearly two decades.  As an undergraduate at Harvard University, Kyle actually formed his own consulting firm to provide services to C-level executives at Harvard who were trying to figure out how to leverage this new technology called the World Wide Web.  When the Harvard Expository Writing Program wanted to conduct a four-year study of undergraduate writing at Harvard, Kyle provided them with all of the resources necessary to conduct this study.  In the days before SurveyMonkey, he actually convinced the director of the program that the only reasonable way to conduct the study was online, and he then wrote the code that generated the survey and recorded student responses.  When the program wondered how it would go about analyzing the data, Kyle hired one of his own statistics teaching fellow to assist with the analysis.  In fact, Kyle even supplied the program with promotional items that the study gave away as thank-you gifts to participants!

Kyle drove Lawrence Academy to be one of the first users of Moodle, an open-source learning management system (LMS).  Kyle's encouragement of faculty in using this tool to enhance their pedagogy was so effective that, when he left the school, there were actually more courses on the LMS than the school actually taught.  The success was so wide-ranging that even the clubs at the school had begun using it.

Kyle's innovative spirit eventually led him to study at Babson College, the nation's top-ranked entrepreneurial business program by U. S. News and World Report.  Babson had held this rating for all of the years that the rating has existed.  Kyle leveraged the knowledge gained there to drive costs down at Lawrence Academy.  Initially, this was accomplished by orchestrating a school-wide leasing program that allowed the school's financial office to better budget for ongoing technology expenses.  However, most of the costs were due to a school policy to have computers located within every classroom on campus.  By changing these computers to terminals, Kyle dramatically shrank the institution's expenditures on technology while simultaneously improving the quality and speed of technology workstations across the campus.

At the Essex Agricultural Technical school district, Kyle's efforts reduced school capital expenditures by leveraging the vagaries of Massachusetts state procurement laws to purchase products for the district at pricing lower than the state-negotiated rate.  His work in researching the legal environment around procurement saved the district countless hundreds of thousands of dollars. He also leveraged new policies to achieve a dramatic reduction in the district's telecommunications expenses by achieving federal funding.

At The Hill School, Kyle has continued these efforts.  Currently, Kyle is working on a highly-directional WiFi project that will link the Montgomery County Community College and the school together.  As a result, The Hill School will join PennREN, a statewide network providing network and educational resources.  With this new connection in place, students will be able to speak — through videoconference — to experts on the Harlem Renaissance, China, and more!