Jon

Jon

Founder, Sandhills CTO LLC

I build things. That's the simplest way to describe what I do and why this practice exists. I've shipped nine products as a solo developer — a service management SaaS, a digital signing platform, a freelance pentesting practice with a self-hosted client portal, a phone-as-sensor RF awareness Android app, a hardware-intensive cybersecurity academy, a typing trainer, a Bible reading app, a 135-article content site, and a custom map merchandise store. I run seven production servers with 98 Docker containers. I built a security-hardened LLM gateway with 15,000+ lines of code and an AI-powered server management platform with 100+ tools and 262 tests. Each was built from scratch, increasingly using AI-augmented development — the same hands-on approach I bring to every client engagement.

My conviction is that technology leadership and security cannot be separated. That conviction comes from a 20-year Army career that took me from infantry platoon leader to Special Forces team member to cyberspace warfare officer — roles where high-stakes decisions, imperfect information, and complex operations were the daily norm.

On the education side, I graduated from the United States Military Academy at West Point in 2006. In 2018, I earned an MS in Information Strategy and Political Warfare from the Naval Postgraduate School, where I also completed the Applied Cyber Operations Graduate Certificate through the adversarial techniques track. My AI work started at NPS in 2018, running machine learning projects with PyTorch before any of the current tooling existed.

On the commercial security side, I hold the OSCP (Offensive Security Certified Professional) certification — a rigorous, hands-on penetration testing exam — and I'm a member of the Synack Red Team, a vetted community of security researchers. I also hold CompTIA A+, Security+, and PenTest+ certifications.

Beyond the hybrid LLM gateway, I’ve built and deployed a complete multi-agent AI platform — four specialized agents that communicate with each other, integrate with workflow automation, and operate on schedules with cost controls. This isn’t a prototype; it’s the system I deploy for consulting clients who want AI working inside their business, on their terms.

But what makes this practice different from other technology consultants is simple: when I recommend a tool or a system for your business, I've built systems like it myself. I don't just advise — I've done the work. I know what it takes to get software set up, get people trained, and make things actually stick. Whether your business needs a professional email address on your own domain or an AI system answering your phone at 2 AM, I've worked at every level of that spectrum.

I live in Southern Pines, North Carolina, where I serve as a deacon at my local Baptist church. Southern Pines sits in the Sandhills region — 35 miles from Fort Bragg and an hour from the Research Triangle — which is why the company is called what it's called.

Career

20 years of leadership, building, and problem-solving

Infantry · 7 Years Platoon and company-level leadership, including combat deployments. Learned to make high-stakes decisions with imperfect information and lead people through the hardest conditions imaginable.
Army Special Forces · 8 Years Small-team leadership in ambiguous environments. Developed expertise in planning complex operations, building partner capacity, and achieving objectives with minimal resources. Deployed multiple times.
Cyberspace Warfare Officer · 5 Years Technology leadership at the intersection of military operations and cybersecurity. Program and project management for technical initiatives. Independent ML research at NPS using PyTorch and Jupyter notebooks. This is where the CTO skillset crystallized.
Builder · Ongoing Nine products shipped as a solo developer. Production AI infrastructure including a security-hardened LLM gateway and an MCP framework connecting AI agents to server management. 36 public GitHub repositories spanning Docker, SDR, IoT, penetration testing, and AI/ML tooling.
Technology Advisor · Now Helping established businesses in the Sandhills region get their technology working for them. From professional email setup to AI automation — practical guidance for businesses that have been running well and want to run better.

Education & Certifications

Academic foundation meets hands-on expertise

BS, Military Art & Science United States Military Academy at West Point, 2006
MS, Info Strategy & Political Warfare Naval Postgraduate School, Monterey, 2018
Applied Cyber Operations Certificate NPS, Adversarial Techniques Track, 2018
OSCP Offensive Security Certified Professional
Synack Red Team Vetted security researcher community
CompTIA A+, Security+, PenTest+ Foundational & advanced security certifications

Let's talk about what your business needs.

No pitch, no pressure. Just a straightforward conversation about whether I can help.

Let's Have a Conversation