A Little About Me
I’ve spent much of my life figuring out how things work, why they sometimes don’t, and what might make them better. For more than 25 years, that curiosity found a professional home in technology leadership and enterprise transformation.
I retired in 2026. The curiosity came along for the ride.

The Professional Chapter
My career took me through some fascinating organizations and challenging assignments.
At Amazon, I led an AI transformation of the Accounts Payable platform, bringing large language models and automation into a substantial, real-world operation. Before that, I spent twenty years at NTT DATA, leading major technology and business transformation initiatives across industries and international organizations.
Earlier in life, I served as a Captain in the United States Army, an experience that shaped my views on leadership, accountability, and the importance of taking care of the people you’re responsible for.
Along the way, I earned an MBA from the University of St. Thomas and a degree in Economics from Marquette University.
I enjoyed solving difficult problems, working with capable people, and seeing ambitious ideas become something useful.
I also developed a healthy appreciation for the difference between making progress and making PowerPoint slides about progress.
Looking back, I’m grateful for the opportunities, the colleagues, and the lessons—particularly the ones I didn’t recognize as lessons at the time.
The Current Chapter
Retirement has given me something I’ve wanted more of for years: the freedom to follow my interests without having to justify them on a calendar.
Classical music has long been a favorite. I enjoy listening, exploring different performances and recordings, and learning more about the composers and the music itself.
I enjoy reading, playing chess, running, and cycling. I’m also discovering some new interests, including tabletop games and other pursuits that offer the appealing prospect of being a complete beginner again.
Family is central to my life. I’m fortunate to have a wonderful wife, three adult children, and four grandchildren. Spending time with them is one of retirement’s great pleasures.
I remain fascinated by technology, especially artificial intelligence and its implications for how we live, work, and think. These days, though, I can explore those questions without having to prepare an executive briefing afterward.
Why This Website?
I’ve had jackblair.com since 2021. It began as a professional portfolio and later became the home of my independent advisory work.
Now it’s simply my personal corner of the internet.
I may occasionally write about a book I’ve enjoyed, a piece of music that caught my attention, or something else I’ve been thinking about.
I’m not trying to build an audience or establish a personal brand. I’ve had enough branding for one lifetime.
Mostly, I like the idea of having a place to collect and share a few thoughts along the way.
If you’ve found your way here, welcome.
