An AI advisory practice for non-technical teams
AI tailored to the way you work.
Generic advice only goes so far. ChicagoAI learns your company, your work, and how your team actually produces it — then embeds the AI tools and workflows with the highest impact on your business.
Three kinds of clients. One thing in common: the work runs on judgment.
ChicagoAI closes the gap between the tools and the team. We study how your business actually produces its work — person by person, workflow by workflow — and then rebuild the way AI fits into it: the right platform, configured correctly, with a team trained on its own real work rather than generic demos.
The practice is deliberately small: one senior operator, a few clients at a time. The person who studies your business is the person who advises it — no leverage model, no hand-offs, no junior bench.
Founder- and partner-led services firms
Communications, advisory, public affairs — firms whose deliverable is thinking, writing, and counsel.
Private-equity-backed operating companies
Where reporting, analysis, and client deliverables consume senior time that should go to running the business.
Owner-led small businesses
Where the owner’s week is the scarcest resource in the company — and there’s no analyst bench to hand problems to.
In every case: non-technical teams that already use AI — and know they are only scratching the surface.
Understand the work first. Then change it.
Every recommendation traces back to something we observed in your firm’s actual work. That is the discipline of the process — and the reason the recommendations hold up.
Deep Discovery
We begin where the value is: with your people and your engagements. We sit with each member of the team and map how their work actually happens — then read across the firm’s client work to see the patterns no single person can see.
Role & work deep-dives
One-on-one sessions with each team member: responsibilities, processes, deliverables, where the hours go, and which recurring tasks quietly consume the week.
Engagement & workstream review
A read of your client engagements end to end — workstreams, work products, requirements, and turnaround pressures — to find where leverage compounds.
AI baseline
How each person uses AI today, what they trust it with, and where fluency varies — so enablement meets people where they are.
The Findings Workshop
Discovery culminates in two sittings: a private readout with firm leadership first — the candid version — then a workshop with the whole team, where every recommendation is proven live and the firm leaves knowing exactly what to change.
The Opportunity Map
The specific places in your work where AI creates the most leverage — ranked and prioritized, and honest about where it doesn’t belong.
Live proof
Every recommendation demonstrated on your own documents and deliverables — not canned examples. Watch your work transform in real time.
The Deployment Blueprint
Which platform and plan, how workspaces and permissions should be structured, and what rolls out in which order.
Applied Working Sessions
Here the room flips: we stop presenting and your team starts doing. Seeing what AI can do takes one workshop; working that way every day takes practice — and this is where the practice happens.
Low-stakes practice
Real assignments in a low-stakes setting — the team learns together, troubleshoots together, and builds confidence before it counts with clients.
Function deep-dives
Sessions shaped by what Discovery uncovered — sometimes firm-wide, sometimes built around one function’s specific workflows.
Assets that stay
Templates, prompt libraries, and shared project setups built in session — so the capability stays with the firm, not the consultant.
What you take away.
AI Opportunity Map
A prioritized map of where AI creates leverage across your roles and engagements — and, just as important, where it doesn’t.
Deployment Blueprint
Platform and plan recommendation, workspace and folder architecture, permission design, and a rollout sequence your team can execute.
Firm Playbook
Templates, prompt libraries, and shared project setups built on your actual work product — assets the team uses the next morning.
Usage & Confidentiality Standards
A plain-language policy for how the firm uses AI — one your team can follow and your clients can be shown.
Platform guidance, without the sales pitch.
We advise on the best ways to deploy Claude firm-wide — the right plan for your size, configured so shared work is shared and sensitive work isn’t — and, where it genuinely makes sense, we recommend other tools that solve a need better. We sell advice, not software, so the recommendation is only ever about what serves the firm.
Grounded in your real work
Every recommendation traces back to something we observed in your actual work — never a generic playbook.
Senior-led, always
The person who studies your firm is the person who advises it. No leverage model, no hand-offs, no junior bench.
Built to outlast us
Success is your team working differently without us in the room. Everything we build is designed to be owned and run by the firm.
The same discipline, scaled to fit.
For small and owner-led businesses, there are three ways to engage — each scoped and agreed before work begins.
Learn to use AI, tailored to your business.
We start by understanding how your business runs, then teach you and your team to use AI where it genuinely helps — hands-on, on your own operations, not generic examples.
Workflows rebuilt, with AI inside.
We take the work that eats your week — proposals, reporting, follow-up, the back office — and rebuild it with AI in the loop, documented so it keeps running without us.
Your thorniest problem, worked for you.
Bring the question you haven’t had time to answer. We put AI to work on your own data — pricing, margins, customers, cash — and come back with an answer you can act on.
Run by an operator, not an agency.
ChicagoAI is the practice of Brian Levin. He has spent his career helping teams turn new capabilities into everyday operations — as a venture builder working with large operating companies, and earlier as a senior editor in digital media.
That is the approach here: understand how your work gets done, make the changes that matter most, and leave your team able to run everything without us.
Background and references shared in conversation.
Senior attention, at full strength.
No discovery phases that run a quarter, no leverage model, no handoffs. The person you hire is the person who shows up.
- StructureWeekly engagements, scoped to an outcome — each week ends with something your firm keeps: a capability, a working system, an answer.
- InvestmentAgreed before work begins. No hourly meters, no change orders. Terms are discussed in conversation.
- AvailabilityLimited. Senior attention doesn’t scale — that’s the point. Current availability is shared in conversation.
Tell me what you’re trying to figure out.
I’ll tell you honestly whether I can help — and what it would take.