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10 Questions to Find the Best Chicago IT Company for Your Business

September 9, 2024 by Hector

Home » IT Services » 10 Questions to Find the Best Chicago IT Company for Your Business

Considering the many options you have when looking for a managed IT services and support provider, it is guaranteed that you will find companies that are good, ones that are bad, and ones that are in-between. 

But only one can be the best. 

To find the best Chicago IT company for your business needs, ask yourself these 10 questions:

1. Do They Know All the Latest Technology Options?

We all know that old technology creates clutter and leaves your business exposed to security hazards, but most business leaders especially dislike the process of replacing old technology with new technology. It is extremely difficult to determine which new tech to buy, and when. 

A good IT support provider will know and have an expert opinion on the latest advances and options in business tech. They should assess what you have and provide helpful, proactive advice about other tools and options you can consider. With their help, you can start planning for necessary IT investments with confidence.  

2. Do They Listen to Your Needs?

It is important to note that there is a difference between offering useful advice and setting down prescriptive yet arbitrary rules. Some managed service providers (MSPs) require you to upgrade all your technology simply so that your systems align better with their systems. This practice benefits their business, but not yours. 

While cutting-edge expertise and proactive advice are critical must-haves for all Chicago IT support companies, the best providers will listen carefully to your business needs, goals, and challenges before addressing issues. 

3. Do They Have Wide-Ranging IT Skills?

Of course, listening does no good unless the provider is prepared to help. No matter how many suggestions your IT company makes, they should rarely, if ever, have to call in another MSP to execute on their plans. 

To ensure that the IT provider you choose maintains predictable costs and service levels, verify that they can and will handle everything in-house, including device configuration, onsite support, and around-the-clock security monitoring from their own Security Operations Center (more on that later). 

4. Do They Provide the Support You Need?

Here is a little-known secret: outsourced IT support companies / managed services providers each deliver different services to their customers. 

Every good MSP will handle: 

  • IT network monitoring
  • Patching and updating
  • Cybersecurity trend reporting

But only some will offer additional services, such as: 

  • Business Continuity / Disaster Recovery (BCDR) 
  • Onsite repair and optimization
  • After-hours and weekend support
  • Proactive IT strategic planning 
  • Employee device security (EDR) 
  • Software licensing and vendor management

As you are perusing an IT support company’s wide range of in-house skills, take the time to verify that their offerings precisely meet your top IT needs. 

5. Do They Understand Your Industry?

Not quite sure what your top IT needs are? You can save a lot of time and eliminate headaches by working with a managed services provider in Chicago that fully understands your industry. When your managed service provider knows your industry, they can help you make the smartest, most effective decisions for IT investments and services. 

For example, they will know which vendors offer discounts on business software to nonprofits, and which tools and services comply with HIPAA and SOX mandates. You may also want to find a provider that knows your mission-critical software, including your accounting solution and Microsoft 365, so you have a one-stop shop for hassle-free business IT support. 

6. Can They Prove Their Experience?

But remember: as in all areas of life, not everyone can “walk their talk.” Any Chicago outsourced IT support provider or MSP can say they have experience with your industry and software, but only a few companies have the hard-won expertise you deserve. Not to say that the less experienced companies are bad companies, but none of them will be the best Chicago IT company for your needs. 

Especially if your industry faces strict compliance requirements, make sure that the IT firm you choose can prove evidence of their experience in the form of references like testimonials or success stories. Tip: Make sure their references cover a wide geographical footprint. The larger their reach, the more likely they are to have deep industry and tech experience that meets your exact needs. 

7. Are They Chicago to the Core?

There is, of course, a point at which a provider can have too large of a geographical footprint. To explain this, we will have to briefly cover the MSP industry. 

In general, MSPs / IT support companies come in 3 options: 

  • The one-size-fits-all national chains

These companies provide the MSP basics we discussed earlier, but little else. They are often the companies that require you to upgrade your systems to align with their own, and they offer zero onsite support because they are not located in Chicagoland. In other words, they think a Chicago dog has ketchup on it. 

  • The specialized local experts

These companies provide the basics, plus a mix of the special, added services we listed earlier (and more). The key here is that their people live and work right here in Chicagoland, so you can trust them for onsite support, on demand. This may be even more of a relief to you than knowing that, like you, they will be avoiding Wrigley like the plague during TBOX this December. 

  • The developer-type international firms

These companies are the biggest names in the industry, such as Palo Alto Networks, FireEye, and Kaseya. They may provide IT support to massive, global companies but they are best known for developing the products your company for IT services in Chicago and the national chains use to support your business’s network infrastructure. The international firms are so laser-focused on crafting new technology for IT professionals that they may not even know Chicago has a lake. 

The best Chicago IT company should obviously be as knowledgeable about Chicago as you are. 

8. Do They Actively Protect Your Business 24/7?

There is a big difference between an IT technician who is on call and one who is actively monitoring your business for cyberthreats at all hours. Some IT support providers switch their 24/7 monitoring to an outsourced, global company after hours. Others rely on automation to scan their customers’ networks overnight, using an alarm to notify their on-call tech if the system finds an anomaly. 

The best IT companies keep their own best people on the clock in their own world-class Security Operations Center (SOC) every day and every night: 24/7/365. These companies are the only ones that are actively monitoring your network at all times, just like they said they would. 

9. Will They Come to Your Offices When You Need Them?

The top reason to look for managed IT services in Chicago instead of through a national chain (or an international IT firm) is because they should offer great onsite support. 

IT issues are inevitable, but crawling around on your hands and knees untangling dusty cables in your server closet is not inevitable. If you take the time to ensure the IT company you are working with provides on-demand, onsite services across Chicagoland, you will know you can trust them to come over and roll up their sleeves right when you need them. 

10. Do They Understand You?

    As we said earlier, there are many IT support providers here in Chicago. It you have found a few companies that meet criteria 1-9 on this list and you are trying to determine which one of them is the best Chicago IT company, we recommend that you sign up with the provider you like the most. 

    Whether you trust your MSP for proactive advice or after-hours emergency care (or anything in between), you will want to work with an IT team that you get along with. They should be friendly and encouraging, happy to share great advice and tips, and —most importantly— they should understand what your organization is all about. 

    SWK Technologies: Your Chicago IT Company

    Start your search with one of the top local IT firms serving Chicagoland: SWK Technologies. Since 2012, our local offices have helped Chicagoland businesses achieve their goals with intelligent, targeted solutions along with personalized advice that addresses specific organizational needs. 

    Begin your search for the top IT company in Chicagoland:

    Learn More About Our MSP Services

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