Jason Pyle
Jason Pyle is the Founder and CEO of Pyleiton, LLC, a consulting firm that helps higher education institutions navigate the practical realities of adopting AI and modern technology. He brings more than two decades of experience in software engineering, systems integration, and technical leadership, with deep specialization in higher education. He also serves as Director of Innovation and Technology at Doctums Global, where he leads technical architecture, AI strategy, and integration design for Student Information System implementations.
Jason's career spans the full range of technology leadership — from writing production code to directing organizations of more than 90 engineers — which gives him an unusually grounded view of where technology initiatives actually succeed or stall. He spent over fifteen years at Ellucian, scaling a software development organization from 8 to more than 90 people and delivering enterprise software to hundreds of colleges. At Anthology, as Vice President of Integrations & Developer Relations, he led two integration organizations through the Blackboard merger and drove the strategic transformation of the integrations function.
That background directly shapes how Jason approaches AI in higher education. His focus today is the unglamorous, real-world work of moving from AI experimentation to actual deployment: evaluating tooling, designing implementation architectures, navigating data governance and security, and building AI capability inside institutions that weren't designed with it in mind. He's especially interested in what that looks like for the lean teams and legacy-heavy systems that run most community and technical colleges — and for the people who keep them running.
Jason has also taught computer science and programming as an Adjunct Instructor at Wake Technical Community College, including courses such as Computing Fundamentals and C++. He holds a B.A. in Mathematics with a minor in Computer Science from McDaniel College and an M.S. in Software Engineering from George Mason University.