About

Why I built
JR Key Advisory.

The work, the background, and the conviction behind the practice.

JR Key, founder of JR Key Advisory

Strategy, facilitation, product judgment, and technical fluency.

I’m JR Key, founder of JR Key Advisory, an independent AI strategy advisory practice based in Portland, Oregon.

JR Key Advisory exists for leadership teams with an AI mandate but without the alignment, ownership, and evidence needed to turn that mandate into measurable progress.

I’ve spent more than two decades moving closer to the decisions that determine whether technology creates value.

My path has moved through training, software development, enterprise UX, cross-functional product work, and strategic facilitation. Across that work, the pattern has been consistent: technology creates value when the right people make clear decisions about the right problems, with enough understanding of how the business actually works.

I’ve worked with organizations including Booz Allen Hamilton, McKesson, Fisher Investments, Allstate, AT&T, BAE Systems, CVS, and others. Different industries. Different technologies. Many of the same organizational patterns.

Today, I help leadership teams make better AI investment decisions before they scale implementation.

The gap between mandate and progress.

As AI has become a strategic priority, I’ve watched familiar organizational patterns emerge with new urgency. Mandates without strategy. Strategy without alignment. Alignment without ownership. Pilots that succeed technically but fail to create meaningful business value. Organizations treating AI as primarily a technology initiative when it is equally a leadership, workflow, and organizational challenge.

Those patterns aren’t unique to AI. They’re the same challenges I’ve encountered throughout my career helping organizations navigate change at the intersection of technology, products, and the people who use them. AI has simply made them more visible—and more consequential.

At McKesson, I led the research and design behind a pharmacy intelligence product that contributed to approximately $97 million in first-year savings across 85 customer organizations. At Fisher Investments, I helped design concepts for integrating AI services into internal products. More recently, I presented to more than 140 members of Exiger’s staff on the uniquely human advantage in the age of AI—why judgment, collaboration, and shared understanding become more valuable, not less, as AI becomes embedded in everyday work.

The throughline was never the technology. It was the people doing the work, the customers they served, and the context in which both had to succeed.

That’s why I founded JR Key Advisory.

Technology moves faster than strategic clarity, organizational alignment, and shared ownership. Agents amplify whatever direction they’re given. When that direction is fragmented, AI scales fragmentation. When leadership establishes a clear, owned strategic mandate, AI can scale meaningful business progress.

JR Key Advisory exists because closing the gap between AI mandate and AI progress requires strategic and organizational work, not just technical implementation.

Why this work fits my background.

I’ve worked in environments where technology decisions had to account for real business constraints, complex stakeholders, regulated contexts, and the way people actually do their work.

That includes experience across training, software development, UX program leadership, product strategy, and cross-functional facilitation. Across roles, my work has often been to enter complex environments, understand the context quickly, and help teams create practical clarity. A development background also lets me speak fluently with technical teams: I know what’s actually possible, what’s genuinely hard, and what’s vendor positioning.

AI strategy now requires that same combination: business judgment, human-centered understanding, technology fluency, and disciplined facilitation.

What I believe about AI progress.

I measure AI progress by whether it helps the business become more effective: better decisions, stronger workflows, increased capacity, improved customer value, and more useful work for the people inside the organization.

It’s less about doing the same work with fewer people and more about how we expand and grow with the people we have.

That is why my work starts with leadership decisions before implementation. The goal is to clarify where AI belongs, what is worth investing in, and what evidence should guide the next step.

A personal note.

AI is changing what organizations can do. But it’s also exposing how organizations make decisions.

As AI accelerates execution, the bottleneck shifts. The harder questions become: What matters most? Who owns the decision? Which workflows should change? How will success be measured? And how do you help people adapt as the technology continues to evolve?

That’s where my background fits.

I understand technology well enough to keep conversations grounded in practical business decisions rather than technology for its own sake. I understand UX and product development well enough to keep the focus on the people doing the work and the outcomes the business is trying to achieve. And I understand facilitation well enough to help leadership teams build shared understanding, make explicit decisions, and move forward with confidence.

JR Key Advisory is designed for established mid-market organizations seeking independent strategic guidance before making larger AI investments. My role isn’t to replace implementation teams or enterprise consulting firms. It’s to help leadership establish the strategic direction that allows implementation teams and trusted partners to make better downstream decisions.

Technology will continue to evolve. The organizations that benefit most will be the ones that consistently make better strategic decisions about where AI creates value and how people adapt alongside it.

If that’s the kind of partnership you’re looking for, I’d welcome the opportunity to talk.

Certifications and training.

My training spans human factors, UX, instructional systems design, facilitation, and AI-assisted consulting. The throughline is practical: help leadership teams make better decisions when technology, people, risk, and business value intersect.

A note on scope: JR Key Advisory evaluates strategic, organizational, workflow, workforce and high-level integration conditions. It does not provide legal opinions, regulatory certification, cybersecurity assurance, detailed architecture validation or guaranteed financial outcomes.

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