About

From joint planning to building with AI.

I'm John Lester. I've spent my career as a U.S. Navy pilot and educator, mostly around aviation, strategy, and planning, and I'm now moving into AI work full-time.

The turn happened at the Joint Forces Staff College, where I taught joint planning and strategy to senior officers. When generative AI showed up, I didn't wait for guidance from on high. I wrote the school's first GenAI course, ran hands-on labs for the faculty, founded the National Defense University's AI Community of Practice, and built more than 20 custom tools for the problems I kept seeing in the classroom and on staff.

That grew into a two-year adoption effort. I taught first to build trust, then let the tools follow once people understood what they were looking at. The audience made it hard in a useful way, since senior officers are trained to distrust anything that sounds like a pitch, so nothing survived unless it earned its place. A fair amount did, reaching roughly 150 faculty and staff and more than 500 students.

These days I'm an Aviation Operational Support Force planner at Commander, Naval Air Forces Reserve, and I use GenAI.mil against live planning and staff work. It's a different job, but the hard parts are familiar, like scattered knowledge, work that gets rebuilt over and over, and a lot of people who need to stay pointed in the same direction. That's most of what drew me to AI in the first place.

I build outside of work too, including web and iOS apps, an agent runtime, and a handful of tools my family uses. Working with these tools every day is how I stay up-to-date about what they can and, probably more important, what they can't do.

Now I'm looking to turn all of it, the adoption work, the teaching, and the building, into a new career.

What I bring

A few things I'm good at

Driving AI adoption

I drove AI adoption at a senior military college by proving value before seeking buy-in. I built practical prototypes that showed how generative AI could improve faculty workflows, student learning, and staff productivity, then used those examples to earn leadership support and reduce skepticism. From there, I scaled adoption through instruction and outreach, reaching roughly 150 faculty and staff and more than 500 students, and founded the NDU AI Community of Practice to sustain momentum.

Designing how people learn with AI

I wrote the school's first GenAI course and built the tools that went with it, including reflection coaches, interactive case studies, leader personas, and red-team partners for wargaming, all aimed at making people think harder, not less.

Building the actual software

I design real things, not just slide decks, including custom GPTs, web apps, iOS apps in Swift, AI systems, and a local-first agent runtime. I work with AI tools every day, so I know where they can help and where they become a blocker.

Planning and leading at scale

Years as a Navy pilot, department head, and joint planner taught me to turn a commander's intent into something people can act on, juggle competing priorities, and explain a hard decision to a skeptical room.

The track record

What I've actually done

See the case studies
  • Ran a two-year AI adoption effort at the Joint Forces Staff College, with the education side (a course, workshops, consults) and the tools side built in parallel so each one fed the other.
  • Wrote and taught GenAI 101, the school's first AI course, reaching roughly 150 faculty and staff and more than 500 senior officers and government civilians.
  • Built the Reflections GPTs, reflection coaches that ask hard questions instead of accepting a paragraph. Student writing came back four to ten times longer and a lot more thoughtful.
  • Built more than 20 custom tools over two years, from a classroom planning canvas to a suite of red-team GPTs. Several logged 100+ sessions in a single cohort.
  • Founded the National Defense University AI Community of Practice and wrote the JFSC and NDU AI-use policy, defining responsible use and adoption guidance for a large academic institution.
  • Now I'm an Aviation Operational Support Force planner for Navy Reserve aviation, using GenAI.mil against live planning and staff work.

Experience

Where I've served

  1. Nov 2025 – Present

    Aviation Operational Support Force Planner

    Commander, Naval Air Forces Reserve. Aligning force structure, infrastructure, and people for distributed carrier aviation support, and using GenAI.mil on live staff work.

  2. Sep 2022 – Nov 2025

    Military Faculty, Joint PME

    Joint Forces Staff College, National Defense University. Taught JPME Phase II and independently created and led the college's generative AI adoption initiative.

  3. Dec 2019 – Sep 2022

    Director, Reserve Training & Readiness

    Naval Expeditionary Combat Command. Directed training and readiness for more than 10,000 Reserve sailors.

  4. Jul 2016 – Dec 2019

    Department Head & Instructor Pilot, C-40A

    Fleet Logistics Support Squadron 56. Led 200+ sailors as a department head, instructor pilot, and overwater standardization evaluator.

  5. Apr 2015 – Jul 2016

    Flag Aide

    Commander, Maritime Patrol and Reconnaissance Force. Executive assistant to an admiral, running schedule, protocol, and senior stakeholder coordination.

  6. May 2013 – Mar 2015

    Strike Operations Officer & Tactical Action Officer

    USS Harry S. Truman (CVN-75). Scheduled carrier air operations and stood watch as tactical action officer for the defense of the carrier.

  7. May 2010 – Mar 2013

    Instructor Pilot

    Training Squadron 2. Primary flight instruction in the T-34C and T-6B.

  8. Jun 2007 – May 2010

    P-3C Patrol Plane Commander

    Patrol Squadron 16. Aircraft and mission commander leading an 11-person crew across maritime patrol missions.

Education & credentials

Schooling and ratings

  • M.S., Systems Engineering

    Naval Postgraduate School, 2013

  • B.S., Computer Science

    United States Naval Academy, 2004

  • Joint PME Phase II

    Joint Forces Staff College, National Defense University, 2022

  • Joint PME Phase I

    USAF Air Command and Staff College, 2021

  • Flight experience

    2,656.8 flight hours across the P-3C, C-40A, and Navy trainers. Commercial Multi-Engine license.

  • Security clearance

    Active Top Secret / SCI.

What I'm after

Work where adoption, teaching, and building all matter.

AI adoption and enablement · AI program or product management · Learning, training, and instructional design · Solutions engineering and other build-and-talk roles