Our Origin Story

After watching too many businesses get burned by outsourced support and slow MSPs, our founder started Windswept IT with a radical idea: what if IT support felt supportive?

Founded in 1999, Windswept began as a software company and has since evolved into a leading managed services provider. We are trusted by businesses across Canada and the U.S., a testament to our commitment to quality and customer satisfaction.

We don’t hide behind ticket portals, we don’t outsource, and we don’t treat clients like just another number. We show up, we solve problems, and we stick around.

Headquartered in Ottawa with a satellite office in Toronto, we are deeply committed to providing local support. We understand the unique needs of businesses in different regions, from Ontario to British Columbia. Our goal is to ensure that technology supports people, not the other way around.

🟩 Book a Free Consultation → One call. No jargon. Just clarity on how your current setup stacks up and how we can help.

Based in Canada’s capital, we understand the unique needs of Ontario businesses, from those in the government sector in Ottawa to those in the financial district in Toronto. But our service area spans the entire country.

With boots on the ground in Ottawa and Toronto, we also support clients in Vancouver, Calgary, Montreal, Winnipeg, and across Canada. Whether you’re managing IT from Edmonton or Halifax, our Canadian-based team is ready to support you.

🟩 Need boots-on-the-ground support? →

✅ Real technicians, not offshore scripts

✅ No ticket backlog, we resolve issues, not just log them

✅ Local support with national reach across Canada and the U.S.

✅ Flat-fee pricing (no surprise invoices—ever)

✅ Fast response times (support requests typically answered in under 15 minutes)*

✅ Onboarding without downtime or disruption

✅ Strategic guidance, not just tech troubleshooting

✅ Trusted by dozens of Canadian businesses

✅ Grown through word of mouth and client referrals

*Response time based on internal tracking; may vary by client SLA

🟩 Schedule Your Free IT Assessment → We’ll benchmark your environment and show exactly how we can help.

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“They actually fix problems instead of logging them. When we switched, our users immediately noticed the difference and so did our uptime reports.” — Practice Manager, Ottawa Dental Clinic.

⭐⭐⭐⭐⭐

“Windswept’s team doesn’t feel like a vendor. They feel like a partner. They’re responsive, sharp, and genuinely care about making our systems work for us, not the other way around.” — Director of Operations, Toronto Nonprofit

Our Values

📌 People First: We treat clients like teammates, not tickets.

📌 Clarity Over Jargon: We speak, act quickly, and follow through on our commitments.

📌 Local Expertise: Canadian-based service that understands your context.

📌 Long-Term Partnership: We’re in it for more than one project. We scale with you.

What industries do you serve?

• We support Canadian businesses in healthcare, legal, nonprofits, professional services, and manufacturing, typically companies with 10–200 users.

Where is your team based?

• Our team is entirely based in Canada, with offices in Ottawa and Toronto. We serve clients in Vancouver, Edmonton, Calgary, Montreal, and across Canada, offering both remote and on-site support.

Do you outsource any support?

• No. All of our support is delivered in-house by full-time Canadian technicians. Outsourcing leads to slow, impersonal service, so we don’t do it.

What’s your response time?

• Most support tickets receive a response within 15 minutes. Critical issues are escalated immediately. We monitor systems in real time to resolve many problems before they’re noticed, ensuring that your business operations remain uninterrupted.

Can you work with my internal IT person?

• Absolutely. We often partner with internal IT teams to offload day-to-day support or provide strategic guidance and coverage.

Do you offer in-person support?

• Yes. We provide on-site support across Ontario and scheduled visits for clients in other provinces, including British Columbia, Alberta, Quebec, and beyond.