About
Jason Swafford
Technology executive who builds and leads high-performing global organizations. 25 years of doing the work, not just advising on it.
Current Focus
- AI Transformation
- Engineering Effectiveness
- Technology Leadership
Contact
Background
I started my career at Compuware in 1998, writing mainframe code and eventually leading their Architecture and UX organizations. Over 15 years, I progressed from Technical Lead to Director, building the change methodology I still use today.
In 2013, I joined Cengage as VP of Technology for Gale Research—massive repositories of digitized primary sources serving libraries globally. My scope expanded to include National Geographic Learning and K-12, then Core Platforms, and finally all of Cengage Learning as SVP of Technology.
At peak, I led 300+ engineers across three continents with a $30M budget. I navigated PE ownership, federal compliance requirements, and multiple M&A integrations. I learned what it takes to transform an organization at scale—and what breaks when you try to scale too fast.
Since 2023, I've focused on AI strategy. I've led enterprise AI implementation for a Fortune 500 company, co-founded an AI-first fintech startup, and continued developing the frameworks that guide my approach. I'm using Claude Code and modern AI tools daily—not just advising on them.
Education
BS, Industrial-Organizational Psychology
Central Michigan University
I consider this a significant strength. The combination of I/O psychology training and extensive computer science training at Compuware gives me a unique perspective. I understand both the technical and human dimensions of technology leadership—how systems work and how people work.
Extensive technical training through Compuware's enterprise development programs: mainframe systems, .NET development, software architecture, UX design, and program management.
Philosophy
Trust before metrics
Trust enables teamwork. Without it, nothing else matters.
Perception is data
How stakeholders see technology is as important as any technical metric.
Transparency over insulation
Technology leaders who hide create distrust. Open the black box.
Show, don't tell
Operating experience beats advice. Do the work, then share what you learned.
Let's talk
I'm always interested in conversations about technology transformation, AI adoption, and what it takes to lead through change.
Get in Touch