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AI SOLUTIONS
A conversation about AI for mid-market firms that starts where it should: governance, identity, and infrastructure decisions that long predate the rollout. Frameworks-aware. Vertical-aware. Built for firms in construction, manufacturing, healthcare, legal, accounting, and financial services who can’t afford to let AI policy be a sentence in a handbook.
No obligation. No sales script. No pre-work required.
Most AI risk in mid-market firms isn’t from AI the leadership team bought. It’s from AI the team already turned on.
Copilot licenses get provisioned before sensitivity labels exist. Staff connect their work email to a third-party AI tool that now indexes every attachment they’ve ever sent. A practice manager pastes a patient note into a free chatbot to draft a follow-up. None of these are malicious. All of them are governance failures that look like productivity wins until an underwriter, an auditor, or a regulator asks a question.
The cliché we keep hearing is:
“We have an AI policy.”
The harder question is whether the policy is something the firm operates by — or something the firm produced.
AI in a mid-market firm is an operational decision before it’s a technology one. The firms doing it well aren’t leading with the model. They’re leading with the governance, the identity posture, and the infrastructure decision underneath.
Copilot is turned on. Sensitivity labels are not. Oversharing scans haven’t been run. The firm is one prompt away from having Copilot surface salary spreadsheets, M&A memos, or HR investigation notes to a user who shouldn’t see them. The investment is real; the posture supporting it isn’t.
Employees are using third-party AI tools — ChatGPT, Claude, Gemini, a half-dozen niche tools — without sanction, without guardrails, and often without leadership knowing which corporate data they’ve already indexed. The discovery exercise alone routinely surfaces 15 to 40 AI integrations no one approved.
Compliance-bound firms — healthcare, legal, financial, accounting — get pushed toward public-cloud AI because it’s the path of least resistance. But there are categories of work where inference should never leave the firm’s controlled infrastructure. The question is rarely asked deliberately; the answer is usually “we’ll figure it out later.”
Three categories of engagement, mapped to where firms get stuck:
A structured review of the AI tools already touching the firm’s data, the governance posture supporting them, and the documentation gaps an auditor or insurer would surface. Produces a prioritized remediation plan — what to fix, in what order, and what to formalize.
Copilot deployment with sensitivity labels, DLP, oversharing remediation, and conditional access designed before rollout — not after the first incident. AI Acceptable Use policy build and staff briefing. Scoped to one product (Copilot, internal Claude, custom dashboards) at a time so the rollout has discipline.
For firms that can’t — or shouldn’t — run AI workloads on public cloud. Two delivery models: Private AI Hosting in Isidore’s colocation facility, and On-Premise LLM Deployment for clients who require inference inside their own walls. Both come with optional ongoing management.
AI Solutions engagements are designed for:
If three or more of those describe your situation, the conversation is for you.
In the interest of not wasting your time:
A short working session, end-to-end:
Done by video, in your office, or over a working lunch in Chicago. No deck. No technical pre-work required.
If we identify scoped work we could help with, we’ll send a proposal within 48 hours. If we identify work better suited to another partner — or work the firm should handle internally — we’ll say that directly.
Three things. We assess what’s already running in a firm’s environment and what’s missing from the governance posture supporting it. We deploy AI tools — primarily Microsoft Copilot today, with custom dashboard and agent work where it fits — with the sensitivity labels, identity posture, and DLP controls that should exist before rollout. And we operate private AI infrastructure for clients who can’t run inference on public cloud, either in our Chicago colocation facility or on-premise at the client site.
Both, depending on the engagement. The AI Strategy Conversation is a service — a 30-minute working session with no obligation. Discovery engagements are scoped fixed-fee assessments. Deployment work is project-based. Private AI Hosting and managed on-premise LLM offerings are recurring infrastructure services with monthly contract terms.
That is the most common starting point. Most firms we talk to have AI already in the environment — Copilot licenses provisioned, staff using third-party tools without sanction, or both. Starting after deployment is harder than starting before, but it is the situation we work in most. The first session focuses on what to lock down immediately, what to discover before further rollout, and what to formalize so the next audit or insurance renewal has documented answers.
No. AI Solutions engagements are scoped and contracted independently. Firms with existing IT relationships often engage Isidore specifically for the AI governance, deployment, or private infrastructure work and keep their existing managed services provider for everything else. Co-managed arrangements are common.
One conversation. Concrete next steps. No follow-up pressure.
Available for engagements in Chicago, Naperville, Aurora, Burr Ridge, Schaumburg, and remotely nationwide. Most strategy conversations booked within five business days.
The Isidore Group is a Chicago-based managed services and cybersecurity firm, founded in 2014, serving SMBs nationally with practice areas including managed IT, co-managed IT, cybersecurity, Microsoft 365, Azure, cloud hosting, backup and disaster recovery, compliance readiness, and strategic IT consulting.
We work with growth-stage firms across construction, manufacturing, legal, healthcare, finance, and accounting. Our positioning is not commodity IT support; it is operational maturity and executive advisory. AI Solutions is the firm’s practice for AI governance, deployment, and private infrastructure work. AI Strategy Conversations are conducted directly with leadership teams — not handed off to junior staff.