How to Choose a Managed IT Provider in Chicago

RJ2 Technologies is a managed IT services and cybersecurity provider headquartered in Deer Park, Illinois, in the northwest suburbs of Chicago. The company was founded in 1998 and has served businesses across the Chicago metro since. Its services include managed IT, co-managed IT, network and server infrastructure, backup and disaster recovery, unified communications, and security services. This page explains how managed IT is bought and sold in the Chicago market: what it covers, what it costs, how to evaluate a provider, and what switching one actually takes. Most of it applies no matter who you hire.

What do managed IT services actually include, and what do they not include?

Managed IT services means a provider takes ongoing responsibility for your technology under one recurring fee, instead of billing you by the hour after something breaks. In practice the agreement almost always covers six things: a helpdesk your staff can contact directly, monitoring of servers and network equipment, patching and maintenance, endpoint security, backup, and some amount of on-site support.

Beyond that, providers differ, and the differences are where the money is. The following are commonly included by full-service providers in this market:

• Helpdesk and remote support for day-to-day user problems. Password resets, printers, Outlook, a laptop that will not join the network.
• Monitoring and alerting on servers, firewalls, switches and backup jobs.
• Patch and update management for operating systems and major third-party applications.
• Endpoint protection, meaning antivirus or EDR agents on every machine, centrally managed.
• Backup management, meaning the backups run, get checked, and get restored when needed.
• On-site visits for anything that cannot be fixed remotely.
• Vendor coordination, meaning the provider calls your internet carrier or your line-of-business software vendor so your office manager does not have to.
• Reporting and budget planning, meaning you get told what is aging out before it fails.

The following are commonly excluded and quoted separately, even by good providers:

• Hardware. Laptops, servers, firewalls, switches, access points. Some providers include hardware in a bundled per-user rate. Most do not. Ask which.
• Software licenses. Microsoft 365, Adobe, your ERP, your practice management system. The provider may resell them, but the license cost is yours either way.
• Projects. A server replacement, an office move, a Microsoft 365 migration, new cabling. These are scoped and billed as projects at nearly every provider.
• After-hours and emergency work, unless the agreement explicitly says otherwise.
• Compliance audits and formal assessments. Managed IT can produce evidence for an audit. It is not the same as being the auditor.
• Third-party fees. Carrier circuits, cloud consumption, per-seat security licensing.

If a proposal does not tell you plainly which of those items are excluded, that is not an oversight. Ask for the exclusions in writing before you compare two quotes, because a number that looks 30 percent lower is usually 30 percent smaller.

What is the difference between managed IT, co-managed IT, and break-fix?

Break-fix means you call when something breaks and pay by the hour. Managed IT means a provider owns your technology under a monthly fee. Co-managed IT means you keep your own IT staff and hand a provider the specific parts you do not want to carry.

The three are not tiers of the same thing. They are different operating models, and the right one depends on whether you have internal IT at all.

Break-fix. You pay for hours consumed. There is no ongoing relationship, no monitoring, and no one is responsible for the things you did not think to ask about. It is the cheapest model on paper and the most expensive one in a bad year, because the provider’s revenue goes up when your systems go down. Break-fix still makes sense for very small offices with almost no infrastructure, for one-time projects, and for a second opinion. It stops making sense the moment you have a server, a compliance obligation, or more than roughly ten people who cannot work when the network is down.

Fully managed. The provider is your IT department. They hold the documentation, run the tools, answer the phone, and are accountable for uptime. This is the standard model for companies with no internal IT staff. The trade is that you are dependent on one organization, so how you exit matters as much as how you start. See the switching section below.

Co-managed. You have an internal IT person or a small team. They are good, they are busy, and there are things they cannot cover: 24-hour monitoring, security tooling that costs more than your whole IT budget to license alone, vacation and illness coverage, project surge capacity, and a second set of eyes on architecture decisions. Co-managed lets you buy exactly those and nothing else. It is the fastest-growing model in the midsize market for a plain reason: hiring a second full-time IT person costs more than a co-managed agreement, and the second IT person still cannot cover nights.

Co-managed agreements usually take one of three shapes:

1. Tools and monitoring only. The provider supplies the RMM, EDR, and backup platform and watches the alerts. Your team does the hands-on work.
2. Tier one offload. The provider takes the password resets and printer tickets so your internal person can work on projects instead of interruptions.
3. Escalation and after-hours. Your team runs the day. The provider takes nights, weekends, and anything above their skill ceiling.

Most co-managed relationships that survive have one thing in common: the split is written down. Who owns the firewall. Who has the domain admin account. Who gets paged at 2am. Ambiguity in a co-managed agreement produces the exact outage everyone assumed the other party was watching.

Can you outsource just the IT helpdesk?

Yes, and it is a common arrangement in the Chicago market, but almost no provider sells it as a standalone product to a company they do not otherwise support. Outsourced helpdesk is usually sold either as a co-managed component to a company with internal IT, or as one line inside a full managed agreement.

The reason is practical rather than commercial. A helpdesk that cannot see your systems, cannot change anything, and does not know your environment is a call center that takes messages. To resolve a ticket rather than log it, the desk needs remote access tooling on your machines, administrative credentials, and current documentation. Once a provider has all three, they are effectively running part of your IT whether the contract calls it that or not.

If you are shopping for outsourced helpdesk specifically, the questions that matter are:

• Who picks up? Your own named team, a shared pool, or an overnight desk in another time zone.
• What can they actually do? Reset a password, or rebuild a profile and push a Group Policy change. Ask what percentage of tickets close without escalation.
• What hours are staffed by humans, as opposed to monitored by software that pages an on-call engineer. Both are legitimate. They are not the same product and they should not cost the same.
• Where does a ticket go when it cannot be closed on the phone? If the answer is “we send it to your internal person,” you have bought a switchboard.
• Do they document what they did, in a system you can read.

What do managed IT services cost in the Chicago area, and what drives the number?

Published rates from managed providers in the Chicago metro generally fall between roughly $100 and $250 per user per month for a fully managed agreement, with most small-business agreements landing in the middle of that band. Per-device pricing, where it is used, tends to run roughly $25 to $75 per workstation and $150 to $400 per server each month. These are market ranges compiled from publicly posted provider pricing, not a quote from anyone, and the spread is wide because the services inside the number vary enormously.

Five things drive where a quote lands:

1. What is bundled. The single largest variable. An agreement that includes EDR, email security, security awareness training, backup, and a 24-hour monitored service is a different product from one that includes a helpdesk and antivirus. Compare inclusions before you compare prices. A rate under about $75 per user in this market almost always means monitoring and helpdesk only, with security and backup sold on top.

2. Your environment. On-premises servers cost more to manage than a cloud-only office. A manufacturing floor with machine controllers, a warehouse with handheld scanners, or a clinic with imaging equipment all add specialist work that a 30-person accounting firm does not have.

3. Compliance obligations. HIPAA, PCI, SOC 2, CMMC, or a cyber insurance questionnaire all add documentation, evidence collection, and control requirements. Compliance-driven agreements sit at the top of the range and should.

4. On-site expectations. Included on-site hours, guaranteed on-site response, and how far you are from the provider’s technicians all move the number. Drive time is real cost in a metro that takes 90 minutes to cross.

5. User count and density. Providers have fixed overhead per client. Very small companies pay more per user than large ones. Multiple small sites cost more than one site of the same headcount.

Costs that are easy to miss when comparing quotes:

• Onboarding. A one-time fee is standard, commonly quoted somewhere between one and three months of the recurring fee, covering documentation, tooling deployment, and cleanup of whatever the last provider left. A provider quoting zero onboarding is either absorbing it into the monthly rate or is not planning to do the discovery.
• Term and auto-renewal. Most agreements run 12 to 36 months. Read the renewal clause and the notice period before you sign, not when you want to leave. RJ2’s standard agreement is three years, and new clients are offered a one-year agreement to get to know each other first.
• Rate escalators. Annual increases written into the contract.
• Overage. What happens when you exceed included on-site hours or project hours.
• Offboarding. Some agreements charge for the handover of documentation and credentials. Find out now.

The most useful question to ask about price is not “how much.” It is “what is your pricing model, and what is outside it.” Per user, per device, flat rate, or tiered. Very few providers in this market state their model publicly at all, so a provider who will tell you plainly on a first call is already showing you something about how they operate.

RJ2 prices in four parts rather than one flat number: IT infrastructure, the environment that delivers your data and software; the user community, the standards applied to every employee; consumption, for one-off software or hardware that only certain staff need; and a time-and-materials rate sheet for projects outside the master services agreement.

How do you evaluate a managed IT provider?

Evaluate on four things, in this order: who actually answers, what is contractually promised, what they do themselves versus resell, and how you get out. Price is the fifth thing, not the first, because a cheap agreement with the wrong scope costs more within a year.

Here is a checklist you can take into a sales meeting. Bring it printed. Watching how a provider handles it tells you more than the answers do.

Operations

• Who answers when my staff call at 8am on a Monday, and are they your employee or a subcontractor?
• What percentage of tickets are resolved by the first person who picks up?
• What are your staffed hours, and what happens outside them?
• How many technicians do you have, and how many clients do they cover?
• What was your technician turnover in the last twelve months?
• Will I have a named primary engineer, and how often does that person change?

Contract and accountability

• What is your contractual first-response target, and what happens when you miss it?
• Show me your standard agreement, including the exclusions, before I ask for a quote.
• What is the term, the notice period, and the auto-renewal language?
• What do you charge to onboard, and what do you charge to offboard?
• What is explicitly not included?

Capability, and this is where weak providers get uncomfortable

• Which services on your website do you deliver yourself, and which do you resell or refer out? There is nothing wrong with partnering. There is something wrong with not saying so.
• Is your security operations center your own team, or a partner’s?
• When did you last perform a full test restore for a client, and can I see the report? A provider who cannot answer this quickly is not doing it.
• Show me a redacted monthly report for a client about my size. Not a sample template. A real one.
• Give me the name and number of a client who left you in the last two years. This is the question that separates providers. Almost none will do it. The ones who will are telling you something.
• Who holds the administrative credentials to my systems, and can I be given a copy of them on any day I ask?
• Who owns the documentation about my network? If the answer is anything other than “you do,” you have found the real term of the contract.
• Can I speak to a client in my industry who has been with you longer than three years?

Fit

• Have you supported a company my size, in my industry, with my compliance requirements?
• How far are your technicians from my office, and what is your on-site response expectation?
• What does your first 90 days look like, week by week?

Red flags that are worth walking away over: a quote produced before anyone looked at your environment; a refusal to show the standard agreement until you are ready to sign; pressure to decide before a stated deadline; an SLA written in adjectives rather than numbers; a provider who will not tell you what they do not do; and any provider who badmouths the incumbent more than they describe their own work.

What does switching IT providers actually involve?

A provider transition typically takes two to six weeks from signature to full handover, and most of the work is administrative rather than technical. The parts that go wrong are almost always credentials, licensing ownership, and backup history, not the new provider’s competence.

Here is the sequence, in the order it actually happens.

Before you sign anything with the new provider. Read your current contract. Find the notice period, the auto-renewal date, and any offboarding fee. Missing a 90-day notice window by a week can cost you a year. Do this first, because the notice date determines the whole timeline.

Discovery, week one. The new provider inventories what you have: machines, servers, firewalls, network equipment, cloud tenants, line-of-business applications, internet circuits, and licenses. Expect this to surface things nobody documented. It usually does.

Credentials and ownership, weeks one to two. This is the phase that determines whether the switch is smooth or ugly. The list you need transferred or verified:

• Domain registrar login. Not the incumbent’s account. Yours.
• DNS hosting.
• Microsoft 365 or Google Workspace global administrator.
• The Microsoft partner relationship. If your Microsoft 365 licenses sit under the outgoing provider’s tenant as their customer, the partner of record and the delegated administration relationship both have to move, and licenses may need to be repurchased or transferred. Start this early. It is the single most common source of transition delay.
• Firewall and switch administrative accounts.
• Backup platform console.
• Line-of-business application admin accounts and vendor support PINs.
• Any certificates and their renewal contacts.

Tooling swap, weeks two to four. The old provider’s remote monitoring agent and antivirus come off, the new one’s go on. These conflict, so it is done in a controlled order, machine by machine. Expect one scheduled evening of disruption, not an outage.

Backup, and this is the one people forget. Your historical backups usually live in the outgoing provider’s platform, under their license. You often cannot take that history with you. Decide before you leave whether you need to retain it, and if you do, arrange an export or an overlapping subscription. Once the account closes, the history is generally gone.

Documentation. Ask for it in writing, in the transition clause, before you sign. Network diagrams, IP schemes, application notes, and vendor contacts. Many providers keep documentation in a platform you have no access to. Some hand it over cleanly. Some hand over a PDF export. Some hand over nothing, and there is frequently no contractual obligation forcing them.

The overlap. Plan to pay both providers for part of one month. It is cheaper than a hard cutover that goes wrong on a Monday.

RJ2 runs onboarding as a set of projects agreed in a planning meeting with your stakeholders: the transition from your current provider, installing management tools to audit your systems and network, setting up your people on the ticketing system, project work to bring the infrastructure up to standard, and moving to RJ2’s security tools. Timing depends on your environment and your agreement.

Signs it is time to leave a provider: the same problem recurs and nobody has explained why; tickets close without you knowing what was done; you find out about a failed backup from the person who needed the file; every request becomes a quote; you cannot get a straight answer about what software is protecting your machines; the person who knew your environment left and nobody replaced that knowledge; or the provider has stopped telling you what is coming and only reacts.

Signs it is not: one bad month, one bad technician, or a project that ran over. Those are worth a conversation before they are worth a transition, and a good provider will take that conversation.

What is specific about the Chicago and northwest suburbs IT market?

Two things shape IT buying here more than anywhere else in the region: the industrial and logistics concentration along the O’Hare corridor and the northwest suburbs, and the age of the building stock both downtown and in the suburban office parks. A provider who only knows downtown offices and a provider who only knows plant floors are genuinely different vendors.

The northwest suburbs are an industrial market, not an office market. The northwest suburbs hold one of the densest concentrations of manufacturers, distributors, freight forwarders and customs brokers in the country. Elk Grove Village alone contains the largest industrial park in North America. IT for those businesses is not a room of laptops. It is machine controllers running unsupported operating systems because the machine cost $400,000 and the vendor will not certify a new one, barcode scanners on warehouse wireless, ERP systems that cannot go down during a shipping window, and an office network that has to be kept separate from the equipment network. Ask any provider you are considering whether they have supported plant floor or warehouse environments. Many good downtown providers have not. RJ2 supports warehouse and manufacturing environments, including low voltage cabling, access controls and surveillance cameras alongside the IT network.

Downtown buildings add a layer that suburbs do not have. In older Loop and River North properties, anything involving cabling, risers, or telecom entrance facilities goes through the building’s engineering staff and often a single approved vendor. Certificates of insurance, freight elevator reservations, and after-hours work windows are normal parts of a project schedule. Carrier options can be limited by what is already in the riser. A provider used to suburban buildings where you can drill a wall on a Tuesday will underestimate all of it.

Illinois has two state laws that change IT requirements here.

• The Biometric Information Privacy Act (BIPA, 740 ILCS 14) is the strictest biometric privacy law in the country and it carries a private right of action with per-violation damages. It matters the moment you put a fingerprint or facial recognition time clock on a warehouse wall, which is extremely common in this market. Written consent, a published retention schedule, and secure storage are requirements, not best practice. If you use biometric time and attendance, your IT provider should already know this. Ask.
• The Personal Information Protection Act (815 ILCS 530) sets Illinois breach notification obligations, including notice to the Attorney General above a threshold number of affected residents. Your incident response plan needs to reflect Illinois timelines, not a generic template.

This is background for a buying decision and not legal advice. Ask your counsel how either applies to you.

Geography is a real cost. The metro takes 90 minutes to cross in traffic. A provider in the Loop serving a plant in Elk Grove Village, or a provider in Naperville serving an office in Schaumburg, is pricing drive time into every on-site visit whether the quote itemizes it or not. Ask where the technicians who would serve you actually sit, not where the letterhead says the headquarters is.

Weather and power. Suburban office parks frequently have a single utility feed and a single carrier entrance. Summer storms and winter ice both produce multi-hour outages. That makes two questions worth asking early: what happens to your phones when the power goes out, and how long can you operate if the office is unreachable.

A note on how to read a local provider list. Most “best MSP in Chicago” listicles are published by MSPs, and the publisher is ranked first. This page is published by one too, which is why RJ2 appears in exactly one section below and not at the top of a list.

Where RJ2 Technologies fits, and where it does not

RJ2 Technologies has run managed IT for Chicago-area businesses since 1998. It is headquartered in Deer Park, Illinois, and it keeps a drop-in space at 333 S. Wabash Ave., Suite 2700, in Chicago. The Wabash space is a drop-in working space engineers use when they are downtown. It is not a staffed office and there is no one there to walk in and meet.

The services are managed IT, co-managed IT, IT support and helpdesk, network and server infrastructure, backup and disaster recovery, security services, unified communications, and enterprise and line-of-business application work. Jeff Dann founded the company in 1998 and is Founder and CEO. Shawn Meyer, Director of Professional Services, has been in the industry 30 years, 21 of them at RJ2.

RJ2’s response targets during covered hours are 30 minutes when a service is down for everyone, 1 hour for limited degradation, and 8 hours for routine requests. The remote support desk runs 7:00 a.m. to 9:00 p.m. Monday to Friday and 8:00 a.m. to 5:00 p.m. Saturday, Central Time, and monitoring runs 24/7.

RJ2 is likely a reasonable fit if: you are a Chicago-area business without a full internal IT department, or with one or two internal IT people who need coverage rather than replacement; you want the same provider handling support, infrastructure, backup and security rather than four vendors pointing at each other; and you value a provider that has been operating under the same ownership since 1998.

RJ2 is probably not the right fit if: you want the lowest hourly rate in the market and no ongoing relationship, because break-fix is not the model; you need a provider physically resident in your downtown building; or you are looking for a single specialized product rather than ongoing responsibility for an environment.

To talk to someone: sales@rj2t.com, or 847-303-1194. Existing clients reach support at 847-303-1193.