Contact Four Winds IT
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Four Winds IT is a managed IT services provider based in Sarasota, Florida, supporting 300+ businesses across Southwest Florida and Tampa Bay. We work primarily with healthcare practices, law firms, financial services and CPA firms, and manufacturers.
Most businesses don't leave their IT provider because of one big failure. They leave because of a hundred small ones: invoices nobody can explain, a help desk that never picks up, and contracts that charge for seats nobody uses. We built Four Winds to fix exactly that.
What makes us different:
- Itemized, transparent billing. Every invoice is backed by a monthly report, so you see exactly what you're paying for.
- No seat minimums. You never pay for empty seats or services you don't use.
- No hardware markup or rental. You buy hardware at cost and you own it.
- Direct engineer access. Our main line rings straight to engineers. No phone trees, no ticket-portal-only support.
- 100% US-based team at every tier.
- Your stack, your choice. No cookie-cutter packages.
What we do:
- Managed IT: help desk, monitoring, patching, and network and infrastructure management
- Security: cyber risk reduction, compliance support for HIPAA and other regulated industries, cyber insurance readiness, and backup and recovery
- Cloud: Microsoft 365 licensing optimization, migrations, and secure remote access
- AI Solutions: secure, organization-managed AI and workflow automation that helps your team get more done without putting client data at risk
Not sure what your current IT should cost? Send us a recent IT invoice and we'll show you exactly what you're paying for. No charge, no meeting required. Call us at (941) 315-2380.
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Min project size
$1,000+
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Hourly rate
$150 - $199 / hr
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Employees
10 - 49
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Year founded
Founded 2014
Service Lines
- Cybersecurity
- 20%
- AI Agents
- 10%
- AI Consulting
- 10%
- AI Development
- 10%
- Compliance Consulting
- 10%
No Focus Areas have been added yet…
Industries
- Financial services
- 20%
- Insurance
- 15%
- Legal
- 15%
- Non-profit
- 15%
- Business services
- 10%
- Manufacturing
- 10%
- Medical
- 10%
- Real estate
- 5%
Clients
- Small Business (<$10M)
- 75%
- Midmarket ($10M - $1B)
- 25%
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Our Story
Four Winds IT has served Southwest Florida businesses since 2014 with one belief: the best technology decisions are human ones. Our team of 30+ is 100% US-based, and over 80% of our full-time staff started here as interns. We believe in clear, itemized billing, honest recommendations, and engineers you can actually reach. Today we support 300+ businesses across Southwest Florida and Tampa Bay.
Meet the Team
Dylan BordenVP of Operations
Dylan leads operations at Four Winds IT and chairs the Sarasota AI Business Lab with the Sarasota Chamber. Formerly in national accounts sales at LexJet, he helps local businesses make practical technology decisions, especially around AI.
What Sets Us Apart
Engineers Answer the Phone
Our main line rings straight to engineers. No phone trees, no receptionist gatekeeping, no waiting days on a ticket. When something breaks, you talk to someone who can actually fix it.Billing You Can Actually Read
Every invoice is itemized and backed by a monthly report. No bundled pricing, no seat minimums, and no hardware markup. You buy equipment at cost, you own it, and you only pay for what you use.100% US-Based, Locally Grown
Nobody on our team is offshore, at any level. Over 80% of our full-time staff started with us as interns, so the people supporting you know our clients, our standards, and Southwest Florida.
Contact Four Winds IT
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