IT Consulting
for Growing SMBs

Three things. First, we’ve been Chicago-based and owner-led since 2005 — the people who founded the company still run your account. Most firms our size are owned by a PE roll-up or managed through layers of account reps. Second, we cover managed IT, custom software development, and AI automation under one team, which is rare at our scale. Third, we don’t outsource client work offshore — senior engineers in-house handle everything from helpdesk tickets to Azure architecture. If that matters to you, we’re probably a fit. If you’re looking for the cheapest hourly rate, we’re probably not.

Our core fit is SMBs with 10 to 200 employees and $2M to $50M in revenue — companies that are past the “cousin-who’s-good-with-computers” stage but not big enough to justify a full internal IT department. We also do project-based work (custom software, audits, migrations) for larger organizations when the scope is well-defined. If your company is under 10 users, a lighter-touch provider is probably a better fit, and we’ll tell you so.

Yes — that’s specifically what we’re built for. Most firms pick one lane: either they run infrastructure or they build software, rarely both. CSW does both under one team, which matters when your custom application depends on your infrastructure working right, or when your Azure environment needs to support a bespoke workload. Having the same people design and operate your technology avoids the finger-pointing that happens when strategy and operations live in separate vendors.

With a conversation, not a questionnaire. You call us or submit the contact form, we schedule a 30-minute call to understand what you’re actually trying to solve, and we follow up with a written proposal that includes scope, timeline, and a fixed or capped cost. For managed IT engagements we start with a free IT assessment — we audit your current environment and give you a written report regardless of whether you hire us. No BDR hand-offs, no 4-step “discovery” sales funnel. You’ll hear from a senior team member within 24 hours.