Chicago, Illinois
IT consulting in Chicago, senior from the first call.
Our Chicago office is at 205 N Michigan Avenue, a few minutes from the Loop. We fix Microsoft 365 environments, run the day to day, and help Chicago teams get something real out of AI.
IT consulting Chicago
Almost nobody we meet here is starting from zero. They already have Microsoft 365, they already have a helpdesk of some kind, and they already have a document library nobody fully trusts. What is missing is one senior person who holds the whole picture and can say, plainly, what to fix first and what can wait until next year.
That is the gap this office fills. We work the way a good in house CIO works, with a national bench behind us. Some clients bring us in for one project, a migration or a governance cleanup, and we leave when it is done. Others hand over the whole function and keep two internal people for the things that genuinely need a badge and a desk.
Chicago is a professional services town, and that shapes what lands on our desk. Law firms, accounting practices, insurance brokerages, agencies, and manufacturers running a downtown office with plants somewhere else. Those businesses live inside email, documents, and deadlines. A sloppy Microsoft 365 setup is not an abstract risk to them. It is a partner who cannot find the signed version of a contract twenty minutes before a filing.
What the Chicago team does
You get one senior contact who stays with the account, not a new name on every ticket.
- 01Microsoft 365 consultingMigrations, governance, managed services, and the cleanup work that makes the rest possible.
- 02AI servicesCopilot adoption, AI governance, and automation, built on a tenant that is actually ready for it.
- 03IT consulting & vCIOProject delivery, virtual CIO and CTO advisory, and custom software when the tool does not exist yet.
What Chicago clients actually call about
None of these are hypothetical. They are the reasons the phone rings at the Michigan Avenue office.
- 01
A tenant nobody has owned for three years
Someone set up Microsoft 365 during a growth spurt, that person left, and the settings have been drifting ever since. Guest accounts from a project that ended in 2023, sharing links with no expiry, four Teams that all claim to be the real one. We audit it, tell you what is exposed, and fix it in an order that does not interrupt the business.
GovernanceAccess reviewCleanup - 02
Managed IT services without the ticket mill
Plenty of Chicago providers will sell you a per seat number and a queue. That works until the problem needs judgment rather than a script. Our managed IT services in Chicago put a named senior engineer on the account, so the person who answers on Tuesday already knows why your finance team has that unusual permission model.
Managed ITHelpdeskNamed lead - 03
Copilot, before the licences renew
Leadership bought Copilot, adoption stalled, and renewal is coming. Usually the tool is fine and the ground under it is not: Copilot surfaces whatever a user can already reach, so a messy permission model turns into an awkward discovery. We tighten the foundation first, then run adoption properly so the spend has something to show for it.
CopilotAdoptionAI governance - 04
A downtown office and sites that are not downtown
Chicago companies rarely sit in one building. There is the Loop office, a warehouse near the interstate, a plant downstate, and a dozen people who have not commuted since 2020. Getting the same files, the same security, and the same support to all of them is a design problem, and it is one we have solved many times.
Hybrid workMulti siteSecurity
Office minutes from the Loop
Reply to a new enquiry
No junior handoffs after the sale
Where our team learned this work
Getting started in Chicago
Four steps, no surprises. Most clients are through the first two inside a fortnight.
- 1
A conversation, not a pitch
Thirty minutes on what is actually going wrong and what you have already tried. If we are not the right firm for it, we will say so on that call and point you somewhere better.
- 2
A look at the environment
We review the tenant, the licensing, the permission model, and the support arrangement you have now. You get the findings in plain language, ranked by what costs you money or exposes data, whether or not you hire us.
- 3
A plan with a number on it
Scope, sequence, timeline, and price. Fixed fee for defined projects, monthly for managed work. We tell you what is urgent, what is merely untidy, and what you can safely leave alone.
- 4
Delivery you can watch
Work runs through our CloudGear365 client portal, so you can see status, decisions, and what is coming next without asking for an update. A senior lead stays on the account after go live.
Coverage
The office is downtown, and most of our Chicago clients are within an hour of it. We regularly work with businesses in the Loop and River North, out along the I-88 corridor through Oak Brook and Naperville, north through Evanston and Schaumburg, and in the industrial corridors on the south and west sides where the office is small and the plant is not.
We come onsite when being onsite changes the outcome. Migration cutover weekends, floor walks before a workplace redesign, leadership sessions where the technology budget gets decided. The rest of the time we work the way your team already works, over Teams, because pretending otherwise just adds travel to your invoice.
If you are further out, in Rockford or Peoria or across the line in northwest Indiana, that is still workable and we do it. We will tell you at the start how often you should expect to see us in person, and we will not overpromise a presence we cannot keep.
No. The Chicago office serves clients across Illinois and the wider Midwest, and the firm as a whole works nationally from here and from Denver. Being in the same city is convenient, not a requirement.