Local for the long run – GUARANTEED

Winnipeg-based IT provider 365 Technologies bucks the industry trend by staying local

Fall 2026 · Cover Story · Photos by Tanner Banas

365 Technologies is here to give your company the most precious of commodities – the ability to operate without interruption.

Every part of a business, whether it’s invoicing, payroll, client records, scheduling, contracts, communication and others, runs through technology.

And as a business grows, the scope of each function becomes more complex, making it increasingly difficult – impossible, really – for an internal staff member to handle.

Everything can run smoothly for years, until it doesn’t. Systems don’t get patched, hardware ages out and that’s when a company is vulnerable to a cyberattack.

“When your system goes down and nobody knows how to fix it, that’s lost time, lost productivity, lost money and, perhaps more importantly, reputational damage,” says Michael Anderson, president and CEO of 365 Technologies. “A managed IT service takes care of all of this.”

The good news for the Manitoba business community is you don’t need to go to an international firm to get the IT services you need. Small and medium-sized businesses can outsource their IT requirements to 365.

The Winnipeg-based company is a managed IT services provider that works with small and medium-sized businesses that have “outgrown the boss’s nephew doing IT on the weekends.”

Founded in 2010, it is the outsourced IT company for more than 90 organizations supporting 3,000 managed users across Manitoba and Saskatchewan. Its clients range from companies with a dozen computer users on the low end up to 150 on the high side.

365, which has more than 230 Google reviews, provides 24/7 help desk services, project management, technology consulting, cyber security, backup and disaster recovery.

“We give our clients access to an entire team of IT professionals at a lower cost than if they hired a dedicated internal staff member. It gives them a scalable option as they grow. We’ve had companies start with us at 20 users and they’re at 50, 60 or 80 computer users now,” Anderson says.

“We give our clients access to an entire team of IT professionals at a lower cost than if they hired a dedicated internal staff member. It gives them a scalable option as they grow. We’ve had companies start with us at 20 users and they’re at 50, 60 or 80 computer users now.”

— Michael Anderson, president and CEO
365 Technologies

The managed IT industry is undergoing “massive” consolidation, similar to what’s happening with insurance companies, dental offices and veterinarian clinics, Anderson says. A number of 365’s local competitors have been sold over the last few years and such transactions — despite initial claims to the contrary — have invariably led to changes in the client experience.

The changes are small at first – your account manager leaves. But then they start to grow – the support line is routed somewhere unfamiliar and service tiers are standardized to a national template that wasn’t built with your firm in mind. Then prices change at renewal and you discover that the people making decisions about your technology have never met your staff, the people who have to live with those decisions.

“That’s what happens when you don’t have ownership that’s rooted in the communities that they’re serving. That’s not what we want to be. We’re committed to the communities we serve,” he says.

Anderson doesn’t just talk the talk, he puts it in writing. The “365 Promise” features a local ownership guarantee that’s part of its service agreement with clients. The guarantee enables clients to exit their contract with 365 if the company is sold to a foreign company.

Another reason for outsourcing IT to the experts is cyber insurers are increasingly requiring additional proof for how a company manages its systems, including what security controls are in place, whether backups are tested, even proof that staff have continued security awareness training. If a business can’t meet those standards, premiums go up, coverage gets declined or a claim doesn’t get paid after an incident.

Anderson is adamant about not doing a local “wash” to make it appear that 365 is local if it’s not. There are many companies that used to be Canadian and now have American owners but still wrap themselves in the Maple Leaf. (Hello, Tim Hortons.) He admits ownership isn’t likely something that prospective clients think about when evaluating an IT provider but he wants to change that.

“We’ve all had a great relationship with a company, a restaurant or a store and then something changes and it’s fundamentally different. You’re dealing with a completely different group of people. We put our money where our mouth is. This is our home, this is where we’re invested. These are our communities and our participation in these communities isn’t going anywhere,” he says.

Anderson is quick to note that 365 doesn’t do IT support by the hour or on an ad hoc basis. He much prefers to have clients who are fully on board. By farming out their IT needs to 365, clients are able to focus their attention on what they do best – running their companies and growing them. They can be confident that the people handling the technology know the business behind it and aren’t going anywhere.

“Everything we do is a flat rate per user per month. It’s unlimited support with a very predictable cost. Being in a reactive mode where the only time we hear from clients is when the house is on fire, that wasn’t how we wanted to operate. We don’t profit from our clients’ pain. It’s quite the opposite. When our clients grow, we grow, too. When a client struggles, we feel it. We are profitable when our clients are stable and productive,” he says.

There’s no question the model is working as 365 has seen its annual revenues grow from less than $3 million five years ago to more than $5 million in 2026.

Because its business model has recurring revenue, 365 – which recently moved into 5,000-square feet of newly constructed office space in southeast Winnipeg – is “highly attractive” to private equity firms.

“I get three to five offers a week to buy 365 Technologies,” he says, noting he has turned them all down.

“But I made my company harder to sell. If you’re a private equity group or a U.S.-based company trying to buy 365, all of my customers are free to walk if we sell. I would no longer have any agreements in place for my clients if I sold.”

“We’re local for the long run. Guaranteed.”