Gentry Advisory

Old-school operations discipline, applied to AI.

I'm Ryan Gentry. I spent 16 years leading teams and keeping complex systems running. Now I direct AI the way I directed people: a clear task, the right access, a written plan, and a check before anything goes live.

Open to full-time AI automation and operations roles, and to project work through Gentry Advisory. Currently building Pencils Down.

How I can help

Automate a process.

One repetitive workflow, built with checks, a human approval step where it matters, and a runbook so it outlives the launch.

Build and run AI tooling.

Agents, local and hosted models, and the guardrails around them, built so you can see what they did and stop them if needed.

Join your team.

Full-time AI automation or operations work, remote in the US or hybrid in metro Detroit.