Chicago IT Outsourcing Services

Get the technology, services, and expertise your business needs to thrive

“Jorel was maybe too fast and gave me no excuse for getting back to work :). Wonderful as always!”

Marijo Kleinfelder

Kids Can Do

“ReachOut is on top of the newest technology and communicates this information to my team. I would highly recommend ReachOut IT to other firms.”

Mark McNabola

McNabola Law Group

“House-on-fire emergency handled by Jovy with grace and speed. So appreciative of the helpfulness and knowledge! She literally saved the day.”

Maggie Mayer

Kinnally Flaherty Krentz & Loran, P.C.

“I have dealt with ReachOut for the past few years & have had nothing but successes. They always maintain professionalism in their field of work.”

Chris Shields

Navitas Capital

“I know that if I have a problem and call that the problem will be completely resolved. I enjoy speaking to Jovy to get my problems resolved. She is very patient and kind with me especially since I seem to get confused with the processes involved with the computer”

Sandy

McNabola Law Group

“You guys alerted me of an issue and addressed it all in the span of about seven minutes. Not too shabby!”

Bob Golden

Dowd and Dowd

“Always a quick response from your team. ReachOut follows up quickly and stays on top of issues until they are completely resolved. Great job!”

Maureen Rubino

Goldberg & Schulkin Law Offices

Led by CEO Rick Jordan, a national authority on cybersecurity and business strategy, we deliver security-first, growth-aligned IT with rapid response and lasting results.

HOW WE HELP

Cybersecurity-First
Lock down your systems from day one, with proactive 24/7 monitoring, threat detection, and security reviews. Shield your business with secure backups, employee training, real-time response, and more.

Simplify Compliance
Turn compliance into a competitive advantage. Stay contract-ready, pass audits the first time, and keep focus on your business. Map your systems to major frameworks, including HIPAA, CMMC, and NIST.

Predictable Pricing
Commitment should go both ways. That’s why clients who choose a 3- or 5-year agreement unlock exclusive rates and premium support packages. Get full access to our services at a rate you can rely on.

15 Years

Supporting companies across North America

6,000+

End users rely on us for support and cybersecurity

90%

Tickets are responded to in just 9 minutes

Most IT outsourcing stops at keeping the lights on. We take full accountability for your business results. Your goals drive every recommendation and every service we deliver.

Responsibility is built in. If we don’t fix the issues or deliver the outcomes we promised, you get your money back. No finger-pointing, no excuses, just real guarantees you can count on.

We don’t just maintain what you have. Our team actively looks for ways to improve your systems, eliminate friction, and help your team work smarter at every turn.

From AI-driven efficiencies to unlocking contractual opportunities through compliance, we turn technology into your advantage.