Jack Blair
Enterprise Transformation Advisor
I help senior leaders make better decisions during enterprise transformation. After 25 years owning high-stakes programs — AI implementation at Amazon, M&A integration, ERP consolidation — I know where these initiatives actually break down.
I work selectively with executives who need an experienced, independent perspective: scoped engagements, real problems, and useful judgment from someone who has run the work.
What I Do
AI Implementation Reality Check
Most organizations are still closing the gap between AI ambition and operational reality. I’ve deployed LLM-driven automation at production scale — $219B in payments, 52M invoices, running in production. I know what a credible roadmap looks like and what a proof-of-concept dressed up as one looks like. I help leaders tell the difference before the investment is made.
Transformation Strategy and Program Scoping
High-stakes programs fail most often at the beginning — when the problem is framed wrong, the scope is too broad, or the organization doesn’t have the capacity to execute what it just committed to. I help leaders define the right problem, structure the initiative, and sequence delivery before significant resources are committed.
Program Health and Executive Thought Partnership
When a program is already in motion and something feels off, an independent read is worth more than another internal review. I assess where programs are exposed, identify governance gaps, and give CIOs, CFOs, and COOs a direct, experienced perspective — not a report, a conversation with someone who has owned these outcomes.
How I Work
Most enterprise transformation initiatives fail not because the technology doesn’t work, but because the problem was framed wrong at the start. The tool gets selected before the business case is honest. The scope expands before the organization has the capacity to absorb it. The pilot succeeds and nobody has planned for production.
I start by framing the actual problem — not the one that’s politically convenient or technically interesting. I build governance that forces decisions and keeps programs moving. When something is stuck, I unstick it through clarity.
I care about what holds after the program ends. Operating models, ownership patterns, and systems that run the business when attention moves on. That’s what durable transformation means.
Selectively available. If the work is interesting, it’s worth a conversation.