About
Will Dent — Technology Executive and Strategist
Technology Executive | Engineer | Advisor.
I've spent 25 years on both sides of the table — writing the code and signing off on the budget. CIO, CTO, CMO, President, founder. The through-line isn't the titles; it's that most technology projects don't fail on the technology. They fail because the people funding the work and the people doing it are describing two different things.
Early on I led development of the first purpose-built iPad application for pilots in business aviation — it won a General Dynamics Technology Achievement Award, but what stuck with me was watching pilots actually use it. The thing that works in the cockpit is rarely the thing that demos well.
Today I'm CIO at AIThinkers, where I help companies figure out where AI earns its keep and where it's an expensive distraction. That's mostly operationally complex industries — aviation, aerospace, distribution, manufacturing — with real constraints, real compliance, and real people who know things the system doesn't.
I write here about AI, engineering, and leadership. Mostly about the gap between what's promised and what ships.
Based in Savannah, Georgia.
Operating principles
- Speak both languages.
- Most projects don't fail on the technology — they fail because the people funding it and the people building it are describing two different things. I've written the code and I've sat in the boardroom. Translation is the job.
- AI where it earns its keep.
- A demo is not a deliverable. The bar is a quoting engine that closes deals, a workflow that removes a headcount tax, a model that pays for itself. If it can't be tied to a number, it's a hobby.
- Keep a human in the loop.
- The people doing the work — the dispatcher, the operator, the person closing the deal — usually know something the system doesn't. Build so their judgment is amplified, not overruled. That's not sentiment; it's how you avoid an automated mistake at scale.
- Boring by default.
- New technology is a cost, and somebody carries it at 3 a.m. I'll reach for the interesting tool when it's the right one, and the dull, proven one every other time. You should be able to fire me and have the next person understand it in a week.
- Teams compound.
- Hire for trajectory, not résumé. Fix the feedback loop so people learn in weeks instead of years. The compounding is slow, and then it isn't.
Selected experience
- Chief Information OfficerAIThinkers — Nov 2024–Present
- Senior ConsultantGear Up Digital (a Dently service) — 2024
- Chief Marketing OfficerElevate Aviation Group — 2022–2024
- President & CTOAeroParts Now — 2018–2022
- President & FounderDently — 2011–2021
- Senior Manager, Interactive MarketingGulfstream Aerospace — 1999–2011
GitHub activity
I build in the open. Follow along on GitHub →
Get in touch
For speaking, advising, or a conversation — contact me.
