5 Best IT Companies in Winnipeg That Solve Tech Problems You Didn’t Know You Had
Running a business today means tech is at the heart of almost everything. From troubleshooting and keeping data safe to scaling up and staying connected, information technology keeps things running smoothly.
That’s why so many Winnipeg business owners, including my cousin, turn to IT companies. He even told me that the right IT partner has saved him time, money, and a lot of headaches multiple times.
With that in mind, we rounded up the top IT companies in Winnipeg. Team up with these pros for total peace of mind.
How much do IT services cost in Winnipeg?
In Winnipeg, pricing for IT services typically ranges from $100 to $200 per hour for on-demand support. Managed IT packages start at about $500 per month.
1. Chekkit
Address: 167 Lombard Ave, Suite 500
Phone: +1 888-919-7719
Business hours:
- Mon – Fri: 9 AM – 5 PM
Chekkit makes it easier for businesses to stay connected with customers—their software-as-a-service keeps everything in one spot. We can see why thousands of companies, including Dewey, A3 Realty, and Actsphere, trust them.
We like how their CRM works. It helps track customer details, conversations, and jobs from the first request all the way to the final invoice and payment.
And their Customer Hub allows customers to book services, approve quotes, and request changes in one simple portal. Just keep in mind that we heard their customer support could be better.
For pricing, they offer a Business plan—at $25 per month, you get all the basics like CRM, bookings, and payments. If you want advanced features, like multi-channel messaging and AI responses, the Business Pro plan at $149/month is for you.
Customized support surpasses all similar providers
“My company switched from Podium to chekkit six months ago and we haven’t looked back. Their customized support surpasses all similar providers AND at a substantial savings. Highly recommend to all small and medium-sized companies.” — Bob Runcer, Google Review
Our review count has increased significantly
“I work with Rhino Shield by Georgia Coatings in Atlanta, GA. We’ve been using Chekkit for 5 years now, and there’s a reason!! Chekkit has been such a blessing to use for communication with all of our homeowners (text AND email). We love being able to send multiple texts & emails at the same time, saving us the headache of sending them individually. Our review count has increased significantly, too, thanks to them. We can send out review invitations and schedule them to go out. We love Chekkit!” — Christina Barnum, Google Review
2. 365 Technologies
Address: 555 Plinguet St #200
Phone: (204) 488-3655
Business hours:
- Mon – Sun: 8 AM – 4:30 PM
365 Technologies has been around since 2010, providing Manitoba businesses with reliable IT support and solutions.
Their Fully Managed IT services monitor networks and respond immediately to issues—sometimes even fixing problems before businesses notice them.
We also like the focus they put on security management, offering content filtering, intrusion and phishing prevention, and VPN access. For businesses that put extra emphasis on data protection, this is a huge plus.
And if something goes wrong, they promise unlimited support services, which include remote assistance, onsite services, and a 24/7 help desk.
This safety net will definitely provide added peace of mind. However, consider whether speedy fixes are a must for your business, since we heard about their slow response times from previous clients.
Their service is second to none
“We use 365 Technologies for all our IT needs. Their service is second to none. I get an answer within minutes anytime I have an IT issue. Would suggest them to anyone looking for full-time or even part-time IT support.” — Gibran Ramole, Google Review
Always had fantastic service
“I have always had fantastic service from 365 Technologies and Bryan in particular. Bryan has always solved my computer problems quickly and efficiently. He is always patient with me in my lack of technical knowledge and has not only solved problems but made suggestions and implemented easy & quick ways for me to do something that I didn’t know my computer could do for me! Excellent service always!” — Barb Weber, Google Review
3. Avenir IT
Address: 141 Bannatyne Ave, Suite 400
Phone: (204) 289-4384
Business hours:
- Mon – Fri: 7:30 AM – 5 PM
Avenir IT wants to give proactive solutions that will pave the way for smooth operations without constant tech hiccups.
A solid example is their Essential IT Services package, which monitors all your devices worldwide, while also spotting potential problems. They also add a layer of security with managed endpoint detection and response.
For companies that need “always-on” support, they provide Proactive Maintenance, which includes 24/7 remote monitoring. This will help boost staff performance, too, because issues get fixed before slowing productivity.
Of course, no company is perfect—we’ve heard reports of condescending customer support, which might turn some people off. Luckily, they offer a 100% satisfaction guarantee, so if you’re not happy, you can just tell them point-blank.
Now, if you want to test their services at no cost, check out their online promos. Who knows? You might be able to snag a free Cybersecurity Remediation Plan.
Has been responsive to our technology needs
“Avenir has been our IT service and support at Evans Family Law Corporation. I am very happy with the service that Mathieu and his staff provide. Avenir has been responsive to our technology needs, and we are in the process of creating what I hope is a long-term relationship. Mathieu’s commitment to customer service is very high.” — Greg Evans, Google Review
Great team of friendly, helpful, knowledgeable staff
“Avenir IT helped us solve our computer problems, set up our network, securely back up our important data, and protect our company from cybercrime. Professional, quick to respond to problems and inquiries, and a great team of friendly, helpful, knowledgeable staff. I would strongly recommend Avenir It to any business, big or small, as an affordable solution to any IT problems or needs. Thank you, Avenir It.” — Lilac Resort, Google Review
4. Constant C Technology Group
Address: 100 Innovation Dr #260
Phone: (204) 272-1458
Business hours:
- Mon – Fri: 8 AM – 5 PM
Constant C Technology Group has been serving Winnipeg’s business community for over 30 years. For local businesses that want a reliable partner, that kind of history speaks volumes.
A popular offering is their fixed-monthly rate Managed IT Services. Instead of worrying about surprise costs, in-house technicians take care of all network and server needs remotely and on-site.
They also help businesses boost productivity by giving employees real-time access to data via their Cloud Services. This definitely makes team collaboration easier.
Security wasn’t an afterthought here. In addition to security management, they can also take care of ransomware—a big reassurance in today’s cyber landscape.
This comprehensive suite of services sounds pretty sweet, but just remember, quality IT solutions don’t come cheap.
Consistently been a reliable and trusted IT partner
“We’ve been working with Constant C Technology Group since 2013, and they’ve consistently been a reliable and trusted IT partner. As a company with our own in-house technology expertise, we value partners who can complement our capabilities, and Constant C does just that. Their support is truly 24/7, and when you call, someone actually picks up. They’ve helped us enhance our cybersecurity posture over the years, and their team is responsive, knowledgeable, and easy to collaborate with. It’s a strong relationship built on trust, and we appreciate the way they support our operations while respecting and integrating with our internal team.” — Jason Wallace, Google Review
Thankful to have 24/7 hassle-free assistance
“Professional, reliable, and always replies in a timely manner. I have had multiple situations when the staff at Constant C were patient, friendly, and easily resolved my inquiry. I’m very thankful to have 24/7 hassle-free assistance just a phone call away. Supporting a local Winnipeg tech company is a bonus!” — Margaux Kitsch, Google Review
5. Sytex
Address: One Lombard Ave #1515
Phone: (204) 894-7301
Business hours:
- Mon – Fri: 8:30 AM – 5 PM
Sytex is known for helping local businesses stay secure and efficient in today’s digital world. We like that they don’t just work with one type of client—they cater to accountants, lawyers, non-profits, healthcare providers, and real estate companies.
If you need on-site dedicated computer services, they have a team of specialists that can keep your operations running smoothly and tailor services to fit your company’s needs. The only drawback here is that on-site support can be pricey.
They also do a good job with remote access solutions, offering flexibility, convenience, and cost efficiency. These are perfect for businesses trying to keep up with hybrid or remote work setups.
Don’t be too worried if something goes wrong, hardware- or software-wise—they provide computer repair and ongoing maintenance.
Has been fantastic in handling my IT needs
“Sytex has been fantastic in handling my IT needs. They’re not only highly competent but also incredibly friendly and easy to work with. I’ve had a great experience with their services and would highly recommend them!” — Utko Kamil, Google Review
Exceptional, extremely knowledgeable, and helpful
“Sytex is excellent. If you require IT services, they are exceptional, extremely knowledgeable, and helpful. They helped us establish a major project from the ground up and were instrumental in the successful installation of our IT infrastructure. They have also been providing exceptional service now that the business is up and running. I highly recommend them to anyone looking for IT services.” — Jimmy V, Google Review