Operator-led AI consulting —
Chicago every week, in person.
Milwaukee-HQ. Chicago onsite weekly or bi-weekly, Tues–Thurs. For finance, big law, insurance HQs, and trading desks who need an AI partner who actually shows up — not another deck deck.
Why Chicago operators need a different AI partner.
You're a 90-minute walk from $7T+ in financial AUM.
CME, CBOE, Citadel, Northern Trust, Allstate, CNA, Zurich — your block is denser with regulated capital than almost anywhere on earth. Off-the-shelf AI doesn't understand FINRA, MiFID, NAIC, or what 'audit-ready' actually has to mean.
Big Law lives here.
Kirkland, Sidley, Mayer Brown, Latham, Winston, Jenner. AmLaw 100 partners need AI that respects conflicts, privilege, and the supervisory framework. We've shipped to firms that have all three.
We come to you, not to the conference.
Most AI consulting in Chicago happens at a Loop hotel ballroom or over a Zoom from California. We get on the train, we sit in your conference room, and we leave with shipped systems.
Tuesday-Thursday cadence.
Weekly or bi-weekly Tues–Thurs in Chicago — the working part of the working week. Discovery, training, milestone reviews happen in person; the build work happens remotely. The mix is the point.
What we do in Chicago, by industry.
Finance & Trading
- ›Trade-reconciliation agents with exception triage
- ›Compliance copilot grounded in your firm policy
- ›Surveillance triage to reduce false-positive review burden
Big Law / AmLaw 100
- ›Conflict checks against full firm matter database
- ›Discovery + privilege flagging (first-pass, attorney-verified)
- ›Engagement-letter generation from intake transcripts
Insurance HQs
- ›Claims-intake automation + first-notice-of-loss triage
- ›Underwriting copilot grounded in your appetite + rules
- ›Fraud-signal detection with audit trail
Healthcare & Biotech
- ›Regulatory submission drafting (FDA, EMA)
- ›Clinical-doc summarization with citation chain
- ›Medical-affairs literature monitoring
Hedge Funds & Prop Trading
- ›Research-note synthesis across sell-side + alt-data
- ›Signal-discovery agents on unstructured filings
- ›Earnings-call transcript Q&A against your thesis library
Logistics & Imports
- ›Shipment-doc OCR with HS code suggestion
- ›Customs-clearance prep automation
- ›Exception-handling agents across freight forwarders
Chicago onsite — weekly or bi-weekly, Tues–Thurs.
Chicago is recurring onsite. Discovery, kickoff, team training, and milestone reviews happen at your office Tuesday through Thursday on the cadence we agree to (weekly for active engagements, bi-weekly for retainers, monthly for advisory). The build work happens remotely between visits.
That mix is the point. You get a consultant who walks in the door with your team — and a delivery practice that ships full systems between visits without dragging engagement timelines.
We meet at your office, your conference space, or a coworking room you prefer — your call. Loop, River North, West Loop, Fulton Market, Lincoln Park, Northshore. We come to you.
How each solution lands in Chicago.
A Wisconsin-rooted operator is exactly what your firm doesn't expect — and exactly what it needs.
You've seen the Loop consultancy that talks markets but ships decks. You've seen the West Coast firm that ships software but doesn't get FINRA. The third option — a Wisconsin-rooted operator who exited a multi-disciplinary firm, generated $50M+ in value, served in the Army, and now ships AI systems on a Tuesday–Thursday cadence — is rare. That's the bet. Cleaner posture than coastal, sharper systems than local, and present in person at the rate Chicago actually needs.
What this looks like on the ground.
Common questions from Chicago operators.
How does the Chicago onsite cadence actually work?+
Tuesday through Thursday, weekly or bi-weekly depending on engagement intensity. Advisory retainers usually get monthly half-week visits. Active build engagements usually get weekly visits. You set the cadence; we hold it.
Do you have a Chicago office?+
Operations are run out of Milwaukee. Chicago is onsite — we meet at your office, your conference space, or a coworking room you prefer (Loop, River North, West Loop are standard). The legal entity is registered in Wisconsin; we serve Illinois operators.
Can you work inside our compliance boundary?+
Yes. We've shipped inside FINRA, SEC, ABA, HIPAA, and NAIC-adjacent frameworks. Private models, on-prem inference where it matters, scoped tool access, audit trails — all standard. Most engagements front-load the compliance review so nothing stalls at the end.
Are you SDVOB?+
Yes. Service Disabled Veteran Owned Business. Relevant if your procurement gives SDVOB preference; otherwise it's signal that we operate with discipline.
What's a typical first month look like?+
Week 1: onsite kickoff + discovery in your conference room. Week 2-3: build of the first slice + your team training session. Week 4: first production milestone shipped + supervisor sign-off if applicable. Then we hold the cadence.
Do you work with hedge funds + prop trading specifically?+
Yes. The Chicago trading community is one of the highest-leverage uses of AI agents anywhere — research synthesis, signal discovery, surveillance, transcript Q&A. We don't sell directional ideas; we build the systems that free up your team to find them.