Vol. 0 — The office of Jeremy Cleland
Currently booking · Q3 2026
Est. 2024
From 18D Special Forces medic to fractional Chief AI Officer.
I take ownership of the AI function inside companies that need the decisions made, not just advised on — and I measure whether AI search names your business when a buyer asks for one like it.
- Fractional Chief AI Officer
- M.S. Artificial Intelligence
- 11 years Special Operations
- U.S. Army veteran
The free instrument
Paste any URL and the scanner returns a 0–100 score in under ten seconds, against the same rubric the paid work uses. It is also honest about the signals a single page fetch cannot measure.
A note from Jeremy
Most AI work fails for a reason nobody wants to put in the deck.
A vendor sells a tool. Nobody owns the strategy. Six months later the license is shelfware, and the postmortem blames the model. The model was almost never the problem.
The organizations that get value out of AI have one thing in common, and it is not their tooling budget. Someone senior owns the function. Not a CTO adding it to a full plate, and not a consultancy that delivers a roadmap and leaves before the roadmap meets its first disagreement with reality. An owner who is still there when the decisions get expensive.
I spent fourteen years in uniform, eleven of them in Special Operations as an 18D Special Forces medic, then finished a master's in Artificial Intelligence and started doing this. The transferable part is not the war stories. It is a tolerance for saying "I don't know yet, and here is how we find out" in a room that wants a confident answer.
So the work here is measured, and it is honest about its error bars. If three months of visibility work has not moved anything further than the measurement noise, the report says so. If an assessment concludes you should not be spending on this yet, that is what it concludes. An engagement that can only ever recommend more engagement is a sales document.
The engagements
Three ways to engage.
- AI search visibility measurement and remediation
AI Visibility Lead
Monthly measurement of whether ChatGPT, Perplexity, Google AI Overviews, and Claude name you when a buyer asks for a business like yours, plus the work to fix the reasons they do not.$1,500–$2,500/mo · starts with the AI Visibility Baseline
- AI strategy and advisory consulting
AI Strategic Advisor
An advisory seat for teams already building with AI: a scored roadmap, honest build-versus-buy calls, vendor evaluation, review of what you are shipping, and evaluation criteria your team can run without me.$5,000–$8,000/mo · starts with the AI Adoption Assessment
- Fractional chief AI officer and AI leadership
Fractional CAIO
An embedded Chief AI Officer who owns the roadmap and its results, sits in leadership meetings, makes the vendor and build-versus-buy calls, and implements the pieces where a handoff would kill the work.$10,000–$15,000/mo · starts with the AI Adoption Assessment
The background
14
years in uniform
11
of them in Special Operations
18D
Special Forces medic
2025
M.S. Artificial Intelligence
The operator
Who you're working with.
I am Jeremy Cleland. Fourteen years in uniform, eleven of them in Special Operations as an 18D Special Forces medic, then a master's in Artificial Intelligence in 2025 and a second career building systems that have to work when someone is depending on them.
Special Operations medicine is a useful background for this work for an unglamorous reason: the job is making decisions with incomplete information, under a deadline, where being confidently wrong is the failure mode that costs the most. That is also the job of running an AI function in 2026.
I build as well as advise. The roadmaps I write are constrained by what I know I would have to implement, which tends to keep them honest about what is actually shippable this quarter.
Most AI advisors are strategists who have never shipped a model, or engineers who have never sat in a leadership meeting. The useful part is doing both.
Questions
Asked and answered.
- Which of the three engagements do I need?
- If the problem is that AI answer engines do not name your business, that is the AI Visibility Lead, $1,500–$2,500/mo. If you have a team building with AI and nobody senior checking the plan, that is the AI Strategic Advisor, $5,000–$8,000/mo. If nobody is accountable for the AI function at all, that is the Fractional CAIO, $10,000–$15,000/mo. The first conversation is usually about which one, and the answer is sometimes none of them yet.
- What does it cost, and are the prices published?
- Yes, all of them. The entry engagements are the AI Visibility Baseline at $1,000 and the AI Adoption Assessment at $6,000, both one time. The monthly tiers run $1,500 to $2,500 per month, $5,000 to $8,000 per month, and $10,000 to $15,000 per month. A published price means the first call can be about the problem rather than about whether you can afford the conversation.
- What is a fractional Chief AI Officer?
- A part-time senior executive who owns a company's AI function and answers for what it produces: which use cases get funded, what ships, what gets killed, how it is governed, and what the board hears. The distinguishing feature is decision rights rather than hours. Here the seat is one to two days a week — 50 to 70 hours a month — on a six-month initial term.
- Do you implement, or only advise?
- Both, depending on the tier. The advisory tier is review and judgment with no implementation. The fractional seat includes hands-on work on the pieces where a handoff would kill the work — deployment, evaluations, monitoring, latency, and cost. The visibility tier is measurement plus the profile, schema, and citation work the measurement points at.
- Can you guarantee ChatGPT will recommend my business?
- No, and neither can anyone else. Nobody controls what a model says. What you get is a measurement instrument with a stated error bar, a baseline taken before any work starts, and the same instrument run the same way afterward. If three months of work has not moved anything outside the error bars, the report says so.
- Who is behind ClelandCo?
- Jeremy Cleland. Fourteen years in the U.S. Army, eleven of them as an 18D Special Forces medic, U.S. Army Special Operations, then an M.S. in Artificial Intelligence from the University of Michigan-Dearborn in 2025 and a second career building production machine-learning systems. The practice is remote, based in Michigan, and works across the United States.
Start here
If the problem is real, let's scope it.
Tell me what is stuck. I read every message personally and reply within one business day — including when the honest answer is that you do not need me yet.