IT, Cloud, Cybersecurity, and VoIP under one roof.
Middleground Technologies is an outsourced managed IT service provider. With our expert IT team, processes, and technology, we provide full-service managed IT, VoIP solutions, cloud services, and cybersecurity services.

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Reviews
the project
IT Solutions for Personal Injury Law Firm
"They provide personalized service."
the reviewer
the review
A Clutch analyst personally interviewed this client over the phone. Below is an edited transcript.
Introduce your business and what you do there.
I’m the owner of a small personal injury law firm.
What challenge were you trying to address with Middleground Techologies?
Our firm had general IT issues. We wanted to build a network for our computers as well as connect an independent scanner to our computers. We also needed to address firewall issues.
What was the scope of their involvement?
Middleground came in and looked at our equipment. They recommended equipment changes and suggested equipment that fit our needs. After we agreed on the purchase of equipment, they set a date to deliver the new products and network our systems.
Now, we just call them as needed because we have a monthly plan with them. If we need assistance, we open a ticket, and then one of their team members responds to it.
What is the team composition?
I’ve worked with different people over the years.
How did you come to work with Middleground Technologies?
We ultimately chose them because the owners were wonderful. They explained all of their services at a fundamental level to help an attorney understand IT.
How much have you invested with them?
We’ve spent between $15,000–$20,000 over the years.
What is the status of this engagement?
We started the partnership in the fall of 2016, and it’s ongoing.
What evidence can you share that demonstrates the impact of the engagement?
They only recommend what we actually need. Their team doesn’t upsell us or do more than needs to be done. They’re trustworthy.
How did Middleground Technologies perform from a project management standpoint?
Their communication’s excellent, and we’ve never had a problem with them. If the person who initially opens our ticket doesn’t know how to fix the problem, they contact one of the owners who always have a solution.
What did you find most impressive about them?
They provide personalized service. If there’s an issue, we contact them and don’t feel like one of 1,000 customers. We can always get a hold of Middleground’s owners, which is important to us. We have a nice working relationship.
Are there any areas they could improve?
No, they’re excellent for our needs.
Do you have any advice for potential customers?
Build a relationship with the owners. If let them come into your business, they’ll better understand your IT needs. It will help you to form a positive working relationship.
the project
Managed IT Services for Digital Marketing Agency
"They are reliable and smart partners to have to grow and scale a business."
the reviewer
the review
The client submitted this review online.
Please describe your company and your position there.
I'm the founder of a consumer brand oriented digital marketing agency.
For what projects/services did your company hire Middleground Technologies?
We have a complex set of needs around data, cybersecurity, and equipment that we turned to the team at Middleground for. We know that security is important and wanted a firm that had expertise and knowledge in the space and could be proactive in helping us with our needs.
What were your goals for this project?
Our goals were to receive and act upon strategic advice around cybersecurity and our equipment and software.
How did you select Middleground Technologies?
We evaluated a number of firms due to our network and found that Middleground offered a personalized experience, had curiosity around our business, and was genuinely interested in providing the right solutions to our business.
Describe the project in detail.
MI provides advisory services for our equipment and cybersecurity needs.
What was the team composition?
The team is outstanding and is lead by one of the cofounders.
Can you share any outcomes from the project that demonstrate progress or success?
We have been pleased by the strategic advice and proactive communication from the team around security and IT related matters. We are fortunate to have a team that we can reach out to that knows what they are talking about in plain language and gives us actionable items to execute to manage our IT and also turn for help when we need it (with a fast response time).
How effective was the workflow between your team and theirs?
Awesome - the communication is efficient, timely, and proactive.
What did you find most impressive about this company?
Proactive, curiosity, thoughtfulness, expertise without the upsell. They are reliable and smart partners to have to grow and scale a business.
Are there any areas for improvement?
Not that I can think of.
the project
Managed IT Services for Law Firm
“They have integrity and provide exceptional service.”
the reviewer
the review
A Clutch analyst personally interviewed this client over the phone. Below is an edited transcript.
Introduce your business and what you do there.
I’m a legal assistant at Touhy Law Group.
What challenge were you trying to address with Middleground Technologies?
Middleground Technologies provides tech support.
What was the scope of their involvement?
In addition to our daily tech support, they’re always available. I need some help, I can call them up and ask a question. So, if I need help setting up a presentation, video conferences, or if I have a question about audio, they’re always there. They make sure that our day-to-day computer use is perfect. If we have a virus or it’s slow, they deal with it right away. They solve any problems we face. They’ve even helped me with computer problems at home. They provide a sense of safety and security when it come to tech.
What is the team composition?
There are 7–8 people I’ve worked with.
How did you come to work with Middleground Technologies?
They’ve been with our company since before I was involved.
What is the status of this engagement?
They’ve been working with us since January 2012, and our engagement is ongoing.
What evidence can you share that demonstrates the impact of the engagement?
We never have computer difficulties because they’re able to solve any issues we face. They have so much knowledge. I can’t say enough how positive of an experience it has been. They do great work and they have great people.
Once, I had a mediation coming up, and I needed to upload audio into a PowerPoint, and I had no idea how it worked. It was after 5 pm, but they helped me work through it. Later, the case went really well too. So, they’ve gone above and beyond to make sure we succeed.
How did Middleground Technologies perform from a project management standpoint?
They have a ticket system, but I can message them directly if needed. They have a 24-hour service, so they’ll get back to me in just minutes, that’s wonderful. They get back to us right away, which can be super important for mediations, before trials, and things like that.
What did you find most impressive about them?
They have integrity and provide exceptional service. They do their work and get the job done.
Are there any areas they could improve?
No, they’re perfect.
Do you have any advice for potential customers?
I don’t really, because I think everything will go well working with Middleground Technologies.
the project
Managed IT Services & Cloud Server Setup for Fast-food Chain
"They put you first, listen, and help. I've never seen a company that is really that compassionate."
the reviewer
the review
The client submitted this review online.
Please describe your company and your position there.
I am the owner of wide range of retail platforms, specially Dairy Queen - where i over see the strategy and executive decisions for the stores.
For what projects/services did your company hire Middleground Technologies?
We needed a company that could manage all of our IT services on a monthly basis, and help us migrate to the Cloud.
What were your goals for this project?
Our goal was to have a new Cloud infrastructure, an IT provider we could rely on to keep us running smooth, and also implement cyber security for us.
How did you select this vendor?
We talked to about 5 different local Chicago MSP's. We chose Middleground Technologies because they were very fast to respond to us - listened to our needs, and put together a plan that just made total sense in English without being overly technical.
They seem to create custom solutions which we liked, and they have a great young dynamic team there.
Describe the project in detail.
We had 10 servers scattered across 6 sites, old computers, no firewalls - in other words, our IT looked like it was from 1995.
Middleground Technologies advised for us to move to the Cloud, and upgrade to new workstations with Windows 10 and Solid state hard drives. We also added new firewalls, ransomware protection, and backups.
What was the team composition?
We started with the sales rep - who setup a series of 4 calls with 3 engineers. We used a creative Google sheet to share between us to keep all tasks assigned and on track. With the calls and the sheet, it was clear who was doing what, and by when it would be completed.
Can you share any outcomes from the project that demonstrate progress or success?
Our Cloud environment is super fast, and we LOVE not having to worry about maintaining servers, and that we can access it from anywhere. Additionally, having Middleground available 24/7 to help us with any questions is a game changer for us. In 2019, after investing into technology, we have seen a 440% ROI from the investment we made.
How effective was the workflow between your team and theirs?
Very seamless - they've done this for 10 years or so, which made it very easy to align with them.
What did you find most impressive about this company?
They really do care. They put you first, listen, and help. I've never seen a company that is really that compassionate.
Are there any areas for improvement?
Can you offer more than just IT services? :)
the project
IT Services for Glass Design Company
"Once Middleground Technologies got everything up and running, it was smooth sailing."
the reviewer
the review
A Clutch analyst personally interviewed this client over the phone. Below is an edited transcript.
Introduce your business and what you do there.
I’m the controller at Glass Designers Inc., a construction company that specializes in glass and glazing for new commercial, industrial, and educational buildings.
What challenge were you trying to address with Middleground Technologies?
We hired Middleground Technologies to keep our network up and running and to ensure everyone had access to the information within our system. Years before, we were working with a smaller IT company that wasn’t backing up our data, and we ended up getting hit with a virus that impacted us for a few months. Middleground Technologies helped us get back on our feet.
What was the scope of their involvement?
Middleground Technologies reorganized our entire network and structure within a few weeks. Their team instructed us on what we needed to do, gave us the antivirus software and backup equipment we needed. In the beginning, they came out to explain specific information to our team because we’re not IT specialists. Since then, most of the communication has been over the phone and done remotely.
What is the team composition?
In the beginning, we worked with one point of contact. After everything stabilized, he assigned a technician to work with us throughout our engagement.
How did you come to work with Middleground Technologies?
About a year before we had our issue with the other company, I started receiving sales emails from Middleground Technologies. At one point, Isaac (Co-Founder & Principal Consultant, Middleground Technologies) called me. He came in with another technician, and together, they diagnosed our entire network, giving us a full report on its health. I was impressed with what they gave us, and that’s how we got started. The other IT company never helped us like that.
How much have you invested with them?
Their average cost with maintenance, virus protection, monitoring, and the lease of servers came to about $1,200 per month.
What is the status of this engagement?
Our engagement with Middleground Technologies started in October 2017.
What evidence can you share that demonstrates the impact of the engagement?
Once Middleground Technologies got everything up and running, it was smooth sailing. From that day forward, we stopped having major IT-related issues. With the other company, we had a problem every six months. The team at Middleground Technologies kept us in line. Currently, we’re subscribed to their telephone service using Microsoft365 and their voice over IP.
When users talk with our help desk, they’re pleased with the answers and services. If they didn’t have an answer right away, they at least called and told us that they were working on the situation.
How did Middleground Technologies perform from a project management standpoint?
From a project management standpoint, the team performs well. When they installed their server, they told us exactly what was going to happen within the timeframe. It worked out the way they said it would. Once that was up and running, it was smooth sailing.
What did you find most impressive about them?
I can’t say enough about how helpful and knowledgeable Middleground Technologies’ team is. They’re so informative, letting us know what they could work with and solving our problems. Their team even helped with our QuickBooks.
Are there any areas they could improve?
If they needed to improve on anything, it would be that they might want to put a two-step deal in place for questions. We’re in the construction industry, which means we rarely sit at our desks and at our computers. When they would answer our questions, we wouldn’t receive the responses until we got back to our office.
The new process would involve an email response along with a call or text to the client, letting them know that the situation was resolved or that they’re working on it.
Do you have any advice for potential customers?
I highly recommend Middleground Technologies to everyone. There’s nothing I would tell them to do differently.
the project
IT Implementation for Heating & AC Rep
"They’re usually very responsive, particularly in emergency situations.”
the reviewer
the review
A Clutch analyst personally interviewed this client over the phone. Below is an edited transcript.
Introduce your business and what you do there.
I’m a sales engineer/sales manager for a commercial and industrial air conditioning manufacturer representative. We sell heating and AC units directly from the manufacturer to contractors for large commercial and industrial spaces.
What challenge were you trying to address with Middleground Technologies?
Our company was growing and our IT system was no longer meeting our needs. So, we hired Middleground Technologies to upgrade our system.
What was the scope of their involvement?
They’ve improved our servers and software, implemented a new network, and boosted our network security. They’ve also advised us on purchasing equipment like computers and monitors. Since our first project, they’ve maintained our system and emails remotely and have made on-site visits when necessary. During emergencies, they’re on-call and have even come to our homes when an employee has a network issue.
What is the team composition?
We have a primary point of contact, but since their company has grown, we can call them and whoever is available will help us.
How did you come to work with Middleground Technologies?
One of our customers recommended them to us. Once we met their team, we explained what we were looking for, and it was a perfect fit.
How much have you invested with them?
We’ve spent between $25,000–$50,000.
What is the status of this engagement?
We started working together in April 2017 and our partnership is ongoing.
What evidence can you share that demonstrates the impact of the engagement?
Since we began our partnership, our business has run more efficiently. Before, I managed the IT system with another freelancer, but it wasn’t reliable for us. Now it’s easier to send out quotes and get things done around the office. They’ve also given us very solid advice about what devices would be best for our business, and have helped us get discounts, which we really appreciate.
How did Middleground Technologies perform from a project management standpoint?
They’re phenomenal, and I appreciate their transparency. They’re usually very responsive, particularly in emergency situations. Their team is growing, and there was one instance when they were completely swamped with work and it took them a little longer than normal for them to respond to us. However, they stayed in touch with me, explained what was going on, and still accomplished what we needed before it became an issue. Although that was a challenge, it was a great experience and I was very impressed.
What did you find most impressive about them?
Their transparency and communication are fantastic. They’re always on top of things and let me know if any issues arise.
Are there any areas they could improve?
Normally, I would say that as they add new customers, they need to maintain their communications. However, they’ve proven that they can do that already. Everything with them has been really great.
Do you have any advice for potential customers?
Tell them exactly what you need, and they’ll let you know whether or not they can deliver for you.
the project
IT Services for Financial Planning Company
"They continuously give us feedback to improve and stay on top of the evolving technology in our industry."
the reviewer
the review
A Clutch analyst personally interviewed this client over the phone. Below is an edited transcript.
Introduce your business and what you do there.
I’m the operations, office, and systems manager for a mid-sized financial planning firm.
What challenge were you trying to address with Middleground Technologies?
We had been working with the same IT firm for around 10 years and they couldn’t keep up with our needs as we outgrew them. We hired Middleground Technologies to take over and alleviate a lot of the workload that wasn’t be handled by the previous team. We needed to be on top of our game, as the world of technology is ever-changing, so we needed their team of professionals.
What was the scope of their involvement?
They provide basic IT services, covering all of our bases for daily needs and technology upgrades. If our printer isn’t working or we can’t open a certain file, they serve as a help desk resource. We also just finished upgrading our server with them, too.
As a financial firm, we have to adhere to a lot of compliance requirements, so they’ve been helpful in finding an archiving system. Our firm also needs to have a cybersecurity policy, and Middleground Technologies helped us completely rewrite the documents to actually match the protocols we have in place. They check in regularly to make sure our cybersecurity is up to speed. They’ve come to our office to host a cybersecurity training session, as our business is required to host one of these. Their team has really been an all-inclusive package.
What is the team composition?
They’re a medium-sized staff with about 15 people who support us. I regularly work with about 3–4 people but can speak to whoever is available when I call the help desk.
How did you come to work with Middleground Technologies?
We chose Middleground Technologies after realizing our previous vendor wasn’t able to scale with us, and we needed a more middle-sized firm.
How much have you invested with them?
Annually, we spend around $25,000. We have a monthly fee for the help desk services, and the other projects are one-offs, so the prices vary.
What is the status of this engagement?
We’ve been working together since May 2018.
What evidence can you share that demonstrates the impact of the engagement?
We don’t have any strict metrics, but the quality of their support is top-notch. Their help desk is incredible. Their support has been a huge help for us, especially in the compliance area. Overall, they’ve been awesome.
How did Middleground Technologies perform from a project management standpoint?
In terms of meeting deadlines and scheduling, they’ve done really well. We have quarterly meetings where they meet with us, give us an update on our performance, and run through any details. They are available all the time and can always get into our computers immediately. I am the go-between for our two teams, so it’s easy for them to walk me through a solution.
What did you find most impressive about them?
I really appreciate the quarterly meetings we have. Middleground Technologies makes sure we’re on track with how many tickets we’re submitting and help find solutions to avoid going overboard. They continuously give us feedback to improve and stay on top of the evolving technology in our industry.
I also value their various marketing and phone services they remind us of, even though we don’t need them currently. I’m regularly impressed with their customer service efforts. I know almost all of their team by name and they’re just a great, smart group of people.
Are there any areas they could improve?
The only critique I have is the length of some tasks, but this is more related to the complexity of our industry, not their team.
Do you have any advice for potential customers?
I absolutely recommend working with them. They’re a great team of people to work with.
the project
Server Development & Management for Dental Care Company
“I can trust them to promptly resolve any time-sensitive issue.”
the reviewer
the review
A Clutch analyst personally interviewed this client over the phone. Below is an edited transcript.
Introduce your business and what you do there.
We’re a dental office, and I’m the president of the company.
What challenge were you trying to address with Middleground Technologies?
We had to update our outdated equipment and renew our legacy software.
What was the scope of their involvement?
They had to transport all the information on our old server to a new one, which was a major relocation. This information included important patient files and charts. The team came in to physically manage our equipment and network as well.
What is the team composition?
I had one point of primary contact who oversaw all communications. This was helpful because I didn’t have to repeatedly explain myself.
How did you come to work with Middleground Technologies?
I was looking for a new IT company and was meeting with different businesses. I met with them after finding them on google search, and they seemed affable and fairly-priced. We decided we’d give it a shot with them.
How much have you invested with them?
We’ve spent somewhere around $60,000.
What is the status of this engagement?
Our last engagement lasted from June to July of 2019, but they provide ongoing support.
What evidence can you share that demonstrates the impact of the engagement?
The quality of their work has been excellent. Our newer system is much faster and smoother. There was almost no downtime when they were changing out the systems. Their turnaround time is consistently remarkable.
How did Middleground Technologies perform from a project management standpoint?
If any issue comes up, we shoot them an email, and it’s always quickly resolved. They’ve even taken care of issues over the weekend. They’re great at prioritizing our requests and tasks, because in urgent situations, they’ll call us back in a timely manner—typically, within half an hour.
What did you find most impressive about them?
Their customer service is great. They’re very open communicators, which makes for an easy engagement. They’ll continuously provide us with status and progress updates. I can trust them to promptly resolve any time-sensitive issue.
Are there any areas they could improve?
I can’t think of anything. I’ve never had any issue with them.
Do you have any advice for potential customers?
Maintain open communication and check your emails regularly.
the project
Remote Work and Network Creation for Trade Association
"They're a great team to work with."
the reviewer
the review
The client submitted this review online.
Please describe your company and your position there.
501(c)6 trade association
For what projects/services did your company hire Middleground Technologies?
New network install, new laptops, establish remote work capabilities
What were your goals for this project?
Implement new systems and hardware to support a remote work environment for our staff and upgrade our old network and file management systems
How did you select this vendor?
Previously worked with MGT on some simple network issues, they do good work so i keep going back!
Describe the project in detail.
Installed w new servers, firewalls, data backup, user laptops, and networking for all users. Also added cyber security compliance to manage critical defense information.
What was the team composition?
MGT team
Can you share any outcomes from the project that demonstrate progress or success?
good work
How effective was the workflow between your team and theirs?
very effective
What did you find most impressive about this company?
They know exactly how to design what we wanted in our system, and helped us achieve our goals while helping us keep within our limited budget
Are there any areas for improvement?
nope, They're a great team to work with.
Middleground Technologies accurately evaluated the client’s requirements and executed valuable solutions that satisfied them. A reliable team, they provide cost-effective recommendations according to the client’s needs. The accessibility of leadership ensures a successful partnership.