About TailoredU Academy
TailoredU Academy is a strategic partner for schools and districts navigating AI readiness, governance, and implementation — translating practical education systems experience into responsible AI adoption.
Our Story
Built to meet students and schools where they actually are.
TailoredU Academy was founded in 2012 with a simple idea: meet students and schools where they are. That mission has carried us through every shift in education — from college access, to dual enrollment, to remote learning, to today's AI moment.
Each chapter of our work has been driven by the same question: what do educators and learners need next, and how do we build systems they can actually use?
Kristofer Stubbs, Ed.D.
Credentials
- Ed.D. Educational Leadership & Administration, Point Park University
- M.Ed. Curriculum & Instruction (College Student Affairs), University of South Florida
- B.A. Sociology, Duke University
Dr. Kristofer Stubbs is an education systems strategist with rare end-to-end experience across the K–12 and higher education pipeline. Over the past fifteen years he has advised, led, and built programs at every level a student touches — from elementary classrooms, to high school early-college pathways, to community college admissions, to the central office of one of the country's most high-profile urban districts.
That breadth is the reason superintendents, principals, charter authorizers, and edtech teams trust him to translate AI from buzzword into responsible, implementable systems. He has sat in their seats.
A career built across every level of education:
District Leadership — New Orleans Public Schools
As Director of Strategy & System-Wide Programming, he designed and delivered AI literacy and prompt engineering training for district administrators, built districtwide program management processes, and led cross-department initiatives using data and digital workflow optimization.
High School Early College — Pittsburgh Public Schools
As Director of Early College High School, he led a dual-credit program serving 100+ students annually, implementing technology-enhanced curriculum across 25+ college credit courses and building partnerships with district IT to integrate digital learning platforms.
Charter & Independent Schools — Cristo Rey Tampa
As founding Director of Technology & Systems Integration, he stood up an entire school's technology infrastructure from scratch — devices, networks, procurement, professional development, and instructional integration.
Higher Education — Lone Star College & CCAC
As System Manager for Dual Credit & Early College, he led digital transformation across eight campuses. As Executive Director of Admissions at the Community College of Allegheny County, he modernized enrollment systems (Salesforce, Power BI) and grew dual enrollment participation by 111%, lifting institutional enrollment from -4.43% to +3.65%.
Edtech & Analytics — ABL Schools
As an Enrollment Data Specialist, he built AI-assisted reporting workflows and data visualizations used by school administrators to guide instructional strategy and resource allocation.
Policy — The Florida Senate
As a Legislative Assistant, he supported education policy research and analysis, giving him direct insight into how state-level policy shapes what schools can and can't do.
Few consultants can credibly speak to elementary leaders, high school principals, charter authorizers, district cabinets, community college presidents, and edtech product teams in the same week. Dr. Stubbs can — because he has worked inside each of those rooms.
That is what every TailoredU Academy engagement is built on: lived experience at every level of education, paired with practical AI implementation expertise.