Henry R. Montoya
I'm an operations and technology leader for associations.
I help association teams get their systems working together and actually used, and I think a lot about where AI fits, on trust and evidence, not hype.
I do this professionally through Rakvia (opens in new tab), my operations and technology consultancy.
About
I'm a Marine turned operations and technology leader. For years I've helped mission-driven teams, most recently a national association and a growing set of nonprofits, turn scattered operations into systems they can actually trust and use. I care more about whether something gets adopted than whether it's clever, and I'd rather ship a working system than a slide deck. I'm based in Chicago.
Where I land on AI
AI is a tool, not a strategy. I reach for it when it makes a system more reliable, faster, or clearer, and the system still has to work without it. What I care about most with associations right now is separating where AI genuinely helps operations from where it's just hype.
What I build
- Plumón (opens in new tab) When I needed a cleaner way to turn screenshots into private, step-by-step how-tos for clients, I built my own Mac app. Nothing it captures ever leaves your machine, and I use it in my own client work.
Veterans and the labor market
- Illinois veteran organization map (opens in new tab) A free interactive map of 1,700+ Illinois organizations that serve veterans, built to help people see where the support and the work actually are. Part of an ongoing interest of mine in the veteran economy.
Off the clock
You'll usually find me in VR playing Population One, out dancing Zouk, or building with AI for the fun of it. That last one runs deep: I've wired together my own personal operating system with Claude Code, the workflows and assistants that help me run my days. It's play, and it's how I stay sharp on what these tools can really do.
Reach me
I'm most active on LinkedIn (opens in new tab). Best place to follow along or say hello.