Where does AI actually pay off in your business?
See the opportunities, back the right ones with confidence, and bring your people with you.
It starts with the AI Assessment: two calls, at the level you run the business. You tell me where it’s going and which decisions get it there. I come back with a roadmap: where to build AI in, in what order, and the foundation it all stands on. If it’s worth doing, I stay on a monthly retainer and build it with your team, in the tools you’ve already invested in.
- Your time
- Two calls: ninety minutes, then an hour
- You keep
- A written roadmap
- After that
- Nothing, unless it’s worth building
Two calls, and you know where to start.
Call one: the decisions that run the business.
Ninety minutes on where you want to take the business, and the chain of decisions that gets it there. Every business wins the same way: customers that cost less to win and are worth more over time. What differs is the calls that make that more likely. Which customers to go after. What to quote. Who goes on the work. Which account needs a call before it’s at risk. We map who makes each call, what they decide it on, and what it moves. No prep, no deck.
You don’t need to know how every process runs. That detail comes later, from the people who own each one. You need to know where the calls get made, and you already do.
Call two: your roadmap.
An hour on what to build, and in what order. Which decisions to build the intelligence into first, and what each one needs to see. What you already have to build on. What’s in the way. What to watch as you go.
Most of all, the foundation, scoped by those decisions. The tools you already own, connected. The AI you’re already paying for, consolidated: you decide what stays before anyone adds another vendor. And how your business works, written down so AI knows it. You keep the roadmap in writing.
Then I build it with your team.
If the roadmap is worth building, I stay on a monthly retainer. You don’t need a full-time AI hire to get started, and you don’t need new software: I build in the tools you’ve already invested in. I start with your leadership team, then work directly with the people who run each part of the business: sales, delivery, operations, marketing. In live working sessions, they share their screen and drive while I tell them what to click, what to ask and what to build. They learn it by doing it.
First, the foundation.
We lay the foundation from the roadmap, in four layers. Your data sources: client records, files, email and project history, where they already live. The systems you already own, connected, with one AI setup instead of several. How the work is done and how you sound, written down so AI knows your business. And a named owner for each process. Every process after stands on it.
Then one process at a time, with the person who runs it.
This is where the process detail comes in, from the people who know it best. Client onboarding with your head of delivery. The content pipeline with your marketing lead. We watch how it runs today, cut the steps it doesn’t need, and build AI into what’s left. Fix the process first, then build the intelligence in: put AI on a messy process and you just get the mess faster. The judgment calls stay with them.
Because they build it themselves, the know-how stays in your company instead of leaving with me. They can change it when the business changes, and after a few processes they start spotting the next one before I do.
Between sessions, I’m a message away.
Your team gets a Slack channel with me, so nobody waits for the next session to get unstuck. And you get a strategic advisor on call: when a vendor pitch, a new tool or a board question about AI lands on your desk, you can think it through with me before you commit.
What we’ve already built keeps getting better. New AI features arrive every week; most of them are noise. I bring in the ones that genuinely improve a process you run, and leave the hype out. A shared page logs every session, every improvement and everything we’ve built, so the whole team can see where things stand.
And it’s yours.
Everything is built in your accounts, in the tools you already pay for, by your people, with me beside them. No new platform to get locked into. When it’s time for a full-time owner, that might be someone already on your team who learned it working alongside me, or a new hire. Either way, I help you get there and hand it over.

Scott Jennings
For a decade I architected enterprise software. I stood up the architecture team at a global EdTech SaaS, then led systems and data through a company-wide transformation. The hard problem was never the technology. It was that nobody could see how the business actually ran.
Now I’m a Claude Certified Architect, and I’ve built an open-source AI system end to end (IMI). I know what’s buildable, what it costs, and what’s still hype, and I’d rather build it alongside your people than hand you a deck.
Executive Briefs
Short reads for executives deciding what AI is worth paying for, who should own it, and how to hire for it. Free, no signup.
- New
The Decision Chain
Every company knows what a customer costs to win and what one is worth. How to map the decisions that move those numbers, find where the chain breaks, and let that tell you where AI goes first.
Read the brief -
Every AI Budget Is a Bet
Less than one dollar in five of AI spend traces to a measured result. How to price what you already run, and how to place the next bet before you can know how it will pay.
Read the brief -
What You Can’t Rent
Seven in ten companies hiring an AI leader hire no one else. What an internal owner can hold, what only an outside architect supplies, and which one you are missing.
Read the brief -
Five Questions for an AI-Enabled Role
A twenty-minute check on one job posting: did the work change with the tools, or were the tools just added to the work?
Read the brief -
Interviewing for Expertise You Do Not Have
How to evaluate candidates who know more about AI than anyone on your side of the table — without pretending to be a technical grader.
Read the brief -
Before Your AI Hire Starts
What to put in place before day one of an AI ownership role. Half of whether the hire succeeds is decided before they start.
Read the brief
Book call one.
Bring ninety minutes and a candid view of how the big calls really get made.
- Call one
- Ninety minutes. Where the business is going, and the decisions that get it there.
- Call two
- One hour. Your roadmap: which decisions to build AI into first, and the foundation they need.
- You keep
- The roadmap in writing, whether or not we go further.
- Fee
- $1,000
Rather write first?
Got it.
Thanks. I’ll be in touch.