ROB THOMPSONBuilder · Colorado Springs Book a 1-to-1

Retired USAF Master Sergeant · Founder, S2 Technical · Colorado Springs

I turn trial and error into systems other people can run.

Twenty years in Air Force communications. Fifteen-plus years shipping production software, ideas and systems. I build and operate platforms with real users and real revenue, lead distributed teams through intent rather than instruction, and write things down so they work without me in the room.

Get in touch See the work

What I bring

Leadership in rules-bound places. Software that has to work.

The Thunderbirds, a service academy, an operational test center, and a 122,000-person public platform all run on the same standard: accountability, written doctrine, and people who can execute it without being told twice.

  • ITechnical leadership in high-consequence environments. Led the communications team for a 135-person squadron; responsible for 115 cadets; commander-level reporting on 23 concurrent programs.
  • IIProduction software, owned end to end. Architecture, build, deployment, automated tests, data pipelines, uptime, support and licensing, on products with real users.
  • IIIAI-enabled engineering in practice. A working method for AI-assisted design, coding, testing and documentation that ships daily, and that I teach.
  • IVCommunication across audiences. Published analysis, a 60-minute framework course, moderator playbooks, and daily writing for thousands of neighbors.

Work

Things I built and still run

Every one of these is live, has users, and pages me when it breaks. Figures are current as of October 2026.

Lead Architect · Administrator · Operator

Apollo and The 411 for the 719

A white-label community and business platform: lead routing engine, verified business directory, civic issue tracker, marketplace and mobile app. Behind it, a civic network across four Colorado Springs communities, self-funded, with 10% of program revenue to an affiliated 501(c)(3). The operating playbook has been adopted independently by other community operators.

PythonFlaskReactPostgreSQLDigitalOceanHerokuNightly pipelinesAutomated tests
the411forthe719.com →
122,000
members across four communities
~400
paying business accounts
~250
verified local businesses receiving routed needs
2013
live and operating continuously since
Founder · Engineer

Odin

Real-estate intelligence that ingests MLS, Freddie Mac and Census data into daily market briefs and affordability models, grown out of Re6 Lab and Redi Data. Its military-housing tool, the PCS Map, covers BAH across 111 installations and was licensed to a military-market brokerage network in 2026.

PythonPandasMLS/RETSFederal datasetsDaily jobs
shouldimovenow.com →
Founder · Engineer

COS Lighthouse

A local-signals and cascade-analysis engine that fuses platform data with federal sources to see what is changing in Colorado Springs before it shows up in the news. Built on the same infrastructure as Apollo.

PythonPostgreSQLFederal APIs
Ask me about it →
Principal · S2 Technical, LLC

Client systems

A HIPAA-compliant operations stack for a healthcare services client, conversational voice-AI deployments for service businesses, and the hosting, uptime and support behind all of them. Integrations across Stripe, Resend, GoHighLevel and DigitalOcean Spaces.

PythonNode.jsReactVoice AInginx
s2technical.com →
Predecessors to Odin · 2016–2021

Re6 Lab and Redi Data

Hyperlocal real-estate statistics and data products for investors, brokers, lenders and title companies. Redi identified more than 220 errors in the regional MLS's own calculations. Both have since been folded into Odin.

PythonStreamlitAngularJava APITableau
Now part of Odin →

Service record

Thirty years, two careers, one method

Enlisted in 1996. Retired as a Master Sergeant in 2016. Shipping software, ideas and systems for fifteen-plus years, starting while still in uniform.

  1. 2016 – now
    Current

    Founder & Principal, S2 Technical, LLCColorado Springs, CO

    Software, data and AI services. Architected and operate Apollo, Odin and COS Lighthouse. Lead a distributed team of remote staff, moderators and contractors through written playbooks. Developed and teach How to Think About Your Thinking, a course on decision-making under uncertainty.

  2. 2013 – now
    Current

    Lead Architect & Administrator, The 411 for the 719Colorado Springs, CO

    Designed the operating system: verification standards, routing rules, moderation doctrine, a consent model for anonymous members, and the economics. Wrote it down so others can run it.

  3. 2022

    Teaching Assistant, University of Denver data bootcampTrilogy Education

    Statistics, Python, databases, front-end visualization, Tableau, Hadoop and applied machine learning. 36 certificates awarded.

  4. 2016 – 2021

    Data AnalystReal estate · Colorado Springs

    Data mining, modeling, financial analysis and dashboards for investors, brokers, lenders and title companies. Built Re6 Lab and Redi Data, the predecessors to Odin.

  5. 2014 – 2016

    Project Manager, AFOTECAir Force Operational Test & Evaluation Center

    Air Force-level test and evaluation oversight of a satellite tracking program with a budget near $1B, reporting to commander level. Built the tracking system that gave the commander one view of 23 concurrent projects.

  6. 2010 – 2014

    Academy Military Training NCOUnited States Air Force Academy

    Responsible for the health, welfare and safety of 115 cadets. Led 2,000 cadets and civilians a year through an experiential leadership course. One of three people in the Air Force certified to run the challenge course.

  7. 2006 – 2010

    Communications Chief, USAF ThunderbirdsAir Demonstration Squadron

    Operations, communications, videography and RF systems for a 135-person squadron deploying worldwide on a schedule that did not move. Directly led 11; led the 7-person team running a $1M prototype communications trailer. Managed global logistics for squadron cargo and personnel.

  8. 1996 – 2006

    Communications & electronics, US Air ForceFairchild AFB · Camp Casey, Korea · Aviano AB, Italy

    Job Control NCOIC running the communications focal point for a 4,000-person base. Installation webmaster at Aviano for several years. Deployments to Iraq (2004), Tunisia and Israel.

How I think

Orientation is the whole game.

I'm a student of John Boyd. The OODA loop gets quoted as "decide fast," but the leg that matters is orientation: holding an approximate picture of reality on the ground and testing it constantly against what you actually observe.

Skip that and you drift from a constructed reality instead of the real one. In the Air Force that cost sorties. In a civic platform it costs trust. In software it costs weeks.

I teach this as a 60-minute framework course, How to Think About Your Thinking, and I run my teams on it: tell people the intent, give them the doctrine in writing, and let them close the loop themselves. If you have a decision you are stuck on, you can book an OODA consult directly.

Lead through intent, not instruction.
Book an OODA consult →
A handwritten notebook page reading: True students of OODA whom practice Boyd's orientation cannot help but orient to the approximate reality on the ground, while continually testing the approximation. Failure to do so results in drift from constructed reality and an OODA failure.
From my notebook

Off duty

The rest of the record

Dad to two amazing young ladies. If you ask them, "being our dad" is the best job I've ever had. I enjoy reading and Krav Maga. I currently live in Colorado Springs; we have been here since 2010. I'm open to roles that stretch what I can do technically, on-site or remote, and I held a DoD Secret clearance from 1996 to 2016 that I'm eligible to re-obtain.

Working stack: Python · Flask · JavaScript · React · Node.js · PostgreSQL · MySQL · MongoDB · SQLAlchemy · Pandas · REST APIs · DigitalOcean · Heroku · nginx · Git · Selenium · Tableau · AI-assisted design, implementation, test generation and documentation

Credentials

  • 2016Retired, USAF Master Sergeant (E-7) after 20 years
  • 2021Data Analytics certificate, University of Denver
  • 2018Full-Stack Web Development, Skill Distillery
  • 2012MBA, Alliant International University
  • 2009BS, Technical Management, Embry-Riddle Aeronautical University
  • 1996–2016DoD Secret clearance, eligible to re-obtain

Contact

Let's talk.

Hiring, a build that needs an owner, or help thinking through a hard decision. Grab time on my calendar, or email. I answer my own.

Book a 1-to-1 OODA consult LinkedIn Resume (PDF)
Email rob@s2technical.com
Phone 719-440-1116
LinkedIn linkedin.com/in/robthompsoncolorado
Company s2technical.com