Working AI systems for 100–500 person companies.
Fractional Chief AI Officer for COOs and CEOs whose teams are still doing the work the AI vendor promised would go away. Plumbing AND adoption — built, run on your team, handed off when I leave.
Book a 30-Minute CallYou’ve probably said one of these in the last 30 days.
- “Why does it take three people to send one proposal out?”
- “Our CRM is a graveyard. I don’t trust anything in it.”
- “I asked for the number three times and got three different answers.”
- “We paid a consultant six figures and there’s nothing left to run.”
- “Everyone says AI. Nobody can tell me what to actually do Monday morning.”
- “The system the last consultant built looks great in screenshots. Nobody uses it.”
None of this is a tools problem. Two things have to be true or AI work fails: the pipes have to actually move data without breaking (plumbing), and your team has to use the thing on Monday without you nagging them (adoption). Most projects solve one and call it done. That’s why you have three abandoned tools in your stack.
What you’re actually hiring me to do.
Stop the bleeding in the seam between sales and ops — or CRM and delivery, or analyst and exec, or wherever the work falls on the floor. Build the piece that should be automated and isn’t. Make sure your team owns it ninety days after I’m gone — not a Notion doc nobody opens.
Same person scopes, builds, and hands off — week one to week sixteen. Built on your existing stack, not a new platform you have to learn.
What this isn’t.
- Not a strategy deck. The deliverable is a working system, not slides about a working system.
- Not a vendor implementation. The vendor’s AI bolts onto broken plumbing. The plumbing gets fixed first.
- Not a head-of-AI hire. No nine-month ramp. Running in week one.
- Not an advisory engagement. The work ships. Your team owns it when I leave.
One way in. Four shapes downstream.
There’s one entry point: the Seam Audit. What happens after that depends on what the map shows.
Seam Audit
You walk into the next board meeting with a printed map of where your operation actually leaks money — and a defensible go/no-go on whether AI is the right answer. Two to three weeks. The map is yours to keep whether or not you hire me for anything else.
How the Seam Audit works →If the map says build — four downstream shapes
Build Sprint
The seam costing you the most stops costing you. Your team owns the fix — documentation, runbook, training, stabilization tail included. Three to ten weeks, sized to scope.
“I know what’s broken. I just need someone to build it and leave it running.”
How the Build Sprint works →Prospecting & Sales Automation
Your sales team stops manually building lead lists. Outbound becomes a system, not a person — built into your existing CRM, not a new platform you’ll need to manage forever.
“My pipeline is healthy but my best people are burning hours building lists.”
How Prospecting works →Productized AI Stack
Your operation runs on the same agent stack I run mine on — in sixteen weeks, not sixteen months. Discovery, build, and a 90-day operator retainer bundled into one fixed-scope SKU.
“I want the result, not the scoping conversation. Show me a SKU and a timeline.”
How the Productized Stack works →Operator Retainer
The same person who built the system is the same person running it. No vendor turnover, no re-explaining context to a new account manager. Monthly, multi-workstream, embedded.
“The system works. Nobody inside the building has the time or depth to keep it evolving.”
How the Retainer works →Seam Audit
- Architecture diagram of your operation, with every people-and-data seam marked — printed, yours to keep
- Seam inventory with what’s leaking through each one (time, money, or trust)
- Prioritized read: which seams to fix first, which can be fixed in a day, which aren’t actually problems
- Go/no-go recommendation — if you can fix it internally, I’ll tell you what to focus on
Not a slide deck of observations. Not a generic audit. A printed map of your operation built on direct examination of your tools, your data, and your workflows. Standalone deliverable — you are not obligated to proceed further.
Build Sprint
- Working system deployed on your stack, integrated with your existing tools, running end-to-end
- Plumbing AND adoption — the data layer and the team-uses-it-daily layer, not one without the other
- Complete documentation and runbook so your team can maintain and extend without calling me
- Training for whoever will own the system internally
- Two-week stabilization tail after handoff — for the tweaks nobody can predict at scope
I work alone. No junior handoffs. I scope it, build it, and hand it off — and the person you talk to in week one is the same person finishing in week twelve. I work in your existing tools; you don’t need new software to work with me.
Working systems in production
I run a multi-agent AI system on my own operation — persistent memory, knowledge graph, governance and safety layers, 75+ integrated tools, running 24/7 since early 2025. When I design AI infrastructure for clients, I’m drawing on what actually runs in production. How it works →
Built an outbound system for an IP attorney targeting general counsels. Day one of the first cohort: 50% acceptance rate. The system handles research, sequencing, and reply routing — the attorney spends his time on conversations, not on list-building. Read more →
A six-person landscaping co-op needed accurate quotes from handwritten site notes and voice memos. Built a custom pipeline — handwriting recognition, transcription, pricing logic, human-in-the-loop. The kind of system SaaS won’t build because the market is too small. Read more →
Earlier engagement, same pattern: at Paytronix, weekly business review reporting ran 14 analyst-hours per cycle. After rebuilding the data plumbing: 3 hours. Eleven hours a week back for actual analysis, every week.
What I actually believe about AI in mid-market ops.
- Big-4 AI engagements optimize for slide volume, not systems that run on Monday. If the deliverable is a deck, you’ve already lost.
- In-house AI hires fail because the plumbing isn’t there for them to inherit. You can’t hire your way past architectural debt.
- Most “AI strategy” is data strategy in a costume. If your CRM is a graveyard, no model will save you.
- Adoption is half the engagement, not a phase 2. Most projects ship working software that no one uses. That’s why I refuse to leave until your team owns it.
- I won’t take engagements where the CEO isn’t the sponsor. Without top-cover, the system gets built and then political-ed to death.
I’m Stuart Wilson. Five-plus years building production data systems at Paytronix — including a reporting infrastructure rebuild that took the team from 14 analyst-hours/week to three. Now I do the same work solo for 100–500 person companies. Same person scopes, builds, hands off. More on how I work →
What does the 30-minute call actually cover?
You describe what’s broken. I tell you whether I’ve seen it before and what fixing it typically involves. We agree on whether a scoped diagnostic makes sense. You leave with a clear next step — even if that step is “not right now” or “talk to someone else first.”
Do I need to have my data in order before we start?
No. If your data were in order, you wouldn’t need me. The Assessment is specifically designed to work from your current state — messy pipelines, inconsistent KPIs, and all. I’ve never walked into an environment that was too broken to assess.
Is this one person or a team?
One person. Me. The person who scopes it, prices it, builds it, and hands it off is the same person throughout. No project managers, no junior analysts doing the actual work while I disappear. The tradeoff: I work with a small number of clients at a time and scope tightly.
This isn’t for you if…
- You’re under 100 employees or pre-product-market-fit.
- You want a deck of recommendations, not a system in production.
- You need a team of ten by Monday.
- You want someone to validate a decision you’ve already made.
- You’re buying AI because the board asked, with no operational problem to solve.
- You want a vendor relationship to manage forever, not a system your team owns.
If any of those is you, the 30-minute call won’t lead anywhere productive. Better we both know now.
“Tell me what’s broken. We’ll figure out if I can fix it.”
The first call is a fit conversation. I take roughly one in three. If we’re not a fit, I’ll tell you in the call and point you elsewhere.
Book a 30-Minute Call