Product · Technology · Applied AI

Dan Gentry

Product, Technology & AI Innovation Executive

Thirty years building enterprise software — and the teams that build it. These days I lead product and engineering organizations through the messy, practical work of putting AI to use without losing the people in the process.

Based in Ocala, FL
Dan Gentry

My story

From satellite mainframes to AI teams.

My parents put a RadioShack TRS-80 Color Computer under the Christmas tree in 1980, and I wrote my first BASIC program before the wrapping paper was cleaned up. I've been in computers ever since. At nineteen that meant the Air Force, operating the mainframes that flew weather satellites for the U.S. military. No degree — everything since has been learned by building: a corporate intranet from scratch in the 90s, a four-year run as my own boss in insurance and real estate, then seventeen years at UnitedHealth Group going from developer to senior director, one shipped system at a time.

Today I lead a 35-person product and engineering organization at one of the largest healthcare companies in the country, where my teams run the platforms and I run the operating model — including our first fully AI-integrated development team.

Along the way I gave a TEDx talk, wrote a book, and have hosted a podcast for eight years. The thread through all of it is a distinction I call Machine Work vs. Meaning Work: technology should absorb the repetitive so people can do the human. That's not a slogan to me. It's how I run teams.

I live in Ocala, Florida, with my wife. Five kids and five grandkids later, I have very concrete reasons to care about giving people their time back.

Selected impact

Change that holds up in the real world.

Strategy only counts when teams can execute it and the results show up in numbers. Three examples.

01

Operating model

From a shared resource pool to five focused product teams

Reshaped ownership around products, giving teams clearer accountability and stakeholders a more dependable roadmap.

02

Applied AI

From experimentation to governed team practice

Created the first fully AI-integrated development team and a structured AI Week that turned ideas into practical automation.

03

Delivery

From six-month releases to a one-month cadence

Reworked product engagement and delivery practices to make a complex enterprise organization materially more responsive.

Leadership focus

A systems view of products, teams, and technology.

Product, technology, and AI innovation executive with 30+ years of experience leading enterprise software, data, quality, and engineering organizations through scale, complexity, and change.

Explore the full career history
  • 01Enterprise product strategy
  • 02AI transformation and governance
  • 03Operating model design
  • 04Application modernization
  • 05Data platforms and analytics
  • 06Executive communication

What's next

The role I'm looking for.

I'm looking for a senior product, technology, or AI transformation leadership role — the kind where an organization knows AI matters but needs someone who has actually operationalized it: real teams, real governance, real delivery, not slideware.

I do my best work in complex environments — regulated industries, enterprise scale, organizations mid-change. Healthcare is where I've spent twenty years, but the operating problems I solve aren't healthcare problems. They're scale, trust, and execution problems.

If that's the problem you're hiring for, let's talk.

The next hard problem

Hiring for a hard problem? Let's find out in one conversation whether I'm the right person for it.

Email Dan