I started at Fidelity Investments in 1995. Y2K was already on a Post-it on my desk. Over the 27 years that followed, I led teams through Y2K itself, September 11th, the 2008 financial crisis, the 2020 work-from-home shift, and three smaller regulatory earthquakes most outsiders never heard about.
By the end, I was running operational risk for Fidelity's investment management company — a 300-person organization responsible for making sure the firm's people, processes, and technology didn't fail the people who trusted us with their retirement.
People ask me what that background has to do with helping a 15-person nonprofit adopt AI. The honest answer: almost everything.
Big change is never a technology problem
Every crisis I led through had the same shape. The presenting problem was technical or external. The real problem was always the same: the organization's people didn't have a shared understanding of what had just changed, what they should do about it, and who got to decide.
Y2K wasn't a coding problem by 1999 — the code was mostly fixed. It was a coordination problem. Who calls the branch if the ATM goes down? Who's allowed to approve an override? Those are human questions.
AI today is exactly the same. The tools aren't the hard part. The shared judgment is.
Three principles I carry into AI work
- 01Start with what breaks. Every crisis plan began with a real failure mode — not a vision statement. The same goes for AI: don't start with what AI could do, start with what's currently broken about your work.
- 02Name the owner. A risk without an owner is a risk that will find you. An AI tool without an owner is a tool that will quietly rot. Every workflow I help build has a human name attached.
- 03Build the capability to disagree. The best risk teams I led were the ones where a junior analyst could tell me I was wrong — and did. Same with AI: if your team can't tell you when the model is wrong, you haven't adopted AI, you've imported a new single point of failure.
Why I left, and what I'm doing now
I loved my time at Fidelity. I left because the organizations I most wanted to help — small nonprofits, mission-driven teams, university groups — couldn't afford what Fidelity-grade thinking usually costs.
Support Savvy is my attempt to take 27 years of operational judgment and make it accessible to a 12-person team that doesn't have a CTO. The same principles. The same seriousness. Just priced and sized for the missing middle.
“Running risk for a giant taught me the same lesson a small nonprofit will teach you: the hard part is never the technology. It's whether your people know what to do.”
Want to talk about where this fits for you?
Thirty minutes. No pitch, no slides. Tell me where your team is. I'll tell you honestly whether I can help.
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