Small Business IT Services in Winchester, VA

Proactive IT support that keeps your business running — not just fixes when things break. Plans starting at $35/month.

Call Jerry: 540.303.2410
Quick answer: SKTS provides proactive managed IT services for small businesses (1–12 employees) in Winchester VA, Frederick County, and the Shenandoah Valley. Plans start at $35/month per device on a 12-month plan (then month-to-month) and include 24/7 monitoring, patching, antivirus, backup verification, and priority remote + on-site support from MCSE-certified owner Jerry Hickman. Call 540.303.2410 for a free consultation.
Skits in business attire

Hey there, business owners! I'm Skits. Jerry's been keeping small businesses running in Winchester for over 20 years — everything from two-person offices to shops with a dozen employees. He's not the kind of IT guy who talks over your head or tries to sell you stuff you don't need. He'll figure out what actually makes sense for your business, explain it in plain English, and keep things humming so you can focus on what you do best.

Break/Fix vs. Managed IT — What's the Difference?

Most small businesses start with break/fix. Here's why many switch to managed IT — and why it usually saves money in the long run.

Break/Fix (Pay-As-You-Go)

Something breaks, you call, we fix it. Simple enough. But here's the catch — you're always reacting. You don't know what a month will cost you, and by the time you call, the problem's already costing you time, productivity, or both.

Break/fix works fine if your tech needs are light and you're comfortable rolling the dice. But once you've got a few employees, a network, and customer data to protect, the surprises start adding up fast.

Managed IT (Proactive Support)

With managed IT, Jerry monitors your systems, installs updates, runs security checks, and catches problems before they become emergencies. You pay a predictable monthly fee, and most issues get handled before you even notice them.

Think of it like an oil change vs. waiting for the engine to seize. One costs a little every month. The other costs a lot when you least expect it. Plans start at just $35/month — less than most business lunches.

Skits tip

Skits says: I've seen it a hundred times — a business owner calls after a crash, a ransomware hit, or a failed hard drive, and the recovery costs more than a whole year of managed service would have. It's not about fear — it's just math.

6 Reasons Managed IT Makes Sense for Your Business

Here's what you actually get when Jerry's watching over your systems.

Predictable Monthly Costs

No surprise invoices. You know exactly what IT costs each month, which makes budgeting a whole lot easier. Plans start at $35/month per device — and that covers monitoring, updates, and priority support.

Fewer Emergencies

Most of the "emergencies" Jerry sees could've been prevented with regular maintenance. Updates get installed, disks get monitored, backups get checked — all before anything goes sideways.

Faster Response Times

Managed clients get priority support. When something does come up, Jerry already knows your setup, your systems, and your history. That means faster diagnosis and less downtime.

Security You Can Trust

Antivirus, firewall checks, Windows updates, and ongoing monitoring. Jerry keeps your defenses current so you're not an easy target for ransomware, phishing, or data breaches.

Someone Who Knows Your Setup

No call centers. No ticket queues. You're working with one person who already knows your network, your software, and your pain points. That's worth more than any SLA document.

Honest Advice, No Upselling

Jerry will tell you when something's worth upgrading and when it's not. He's not trying to sell you a new server every two years. If your current setup works, he'll keep it working.

"Jerry has been taking care of our business IT for years. He's always responsive, always honest, and he never tries to sell us something we don't need. When we switched to managed service, our downtime dropped to almost nothing. Best decision we made."

— Kevin, Winchester VA

What's Included in Managed IT?

Every managed plan includes these essentials. No hidden fees, no fine print.

  • ✓ 24/7 system monitoring and alerts
  • ✓ Windows and software updates managed for you
  • ✓ Antivirus and security monitoring
  • ✓ Backup verification and recovery planning
  • ✓ Priority remote and on-site support
  • ✓ Network health checks
  • ✓ Quarterly review and recommendations
  • ✓ One point of contact who actually knows your business

View Pricing Plans

Remote Office? Jerry's Your Central IT Hub.

No physical office doesn't mean no IT support. These services are built for distributed teams.

Skits Handyman

Equipment Depot

New equipment ships to SKTS. Jerry configures it, installs your software, joins it to your network, tests everything — then ships it to your employee, ready to go on day one.

Personnel change? Equipment comes back to SKTS. Jerry wipes it, reconfigures for the next person, and ships it out again. No sensitive data left behind.

Skits Network Navigator

Server Hosting

No office for a server? Jerry hosts it at SKTS. Your team accesses it remotely, just like they would in an office. Jerry handles maintenance, backups, updates, and security.

Monthly fee, no surprise costs, no server closet to worry about.

Skits Cyberhero

Secure VPN & Remote Access

Your team needs to access the office server, shared files, and internal tools from anywhere — securely. Jerry sets up VPN connections so your remote employees can work as if they're sitting in the office, with all the security of being on-site.

Encrypted connections, no exposed ports, no shortcuts that put your data at risk.

Skits Cloud

Cloud Collaboration & Conferencing

OneDrive, Google Drive, SharePoint, shared calendars — Jerry sets up your cloud tools so everyone can access, share, and collaborate on the same files from anywhere. No more emailing documents back and forth.

Need Zoom or Teams for meetings? Jerry handles the setup, the accounts, and the training so your team actually knows how to use it.

Skits

Remote offices are the new normal. Jerry's been setting up distributed teams for years — long before everyone else had to figure it out. Whether you've got two remote employees or twenty, he'll build you a system that works like everyone's in the same building. Call 540.303.2410 and let's talk through your setup.

Skits in business attire

Let's Talk About Your Business

No pressure, no contracts to sign on the first call. Jerry will take a look at what you've got, talk through what makes sense, and give you a straight answer. If managed IT isn't right for you, he'll say so.

540.303.2410

Specific Services Small Businesses Call Us For

Beyond the managed plan, here are the calls that come in most often.

Virus & Ransomware Cleanup

Network-wide cleanup, isolation, prevention setup, and a phishing-awareness brief for your team. Business cleanups are quoted based on size. Free assessment first.

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Data Recovery

Dead drives, accidental deletes, ransomware encryption. Free assessment first — you know what's recoverable and what it'll cost before any work begins.

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Managed Antivirus

$69/yr per computer, $49/yr per phone or tablet. Jerry installs it, monitors it, and handles threats so you don't have to. Real protection — not a trial that expired.

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Staff Training

Group training for your team — phishing & scam awareness, Microsoft 365 onboarding, password & account security, new-software rollouts. Jerry comes to your office; one rate covers the room. Quarterly briefings available.

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Frequently Asked Questions

What does managed IT actually include for a small business?

Every SKTS managed plan covers 24/7 system monitoring, Windows and software updates managed for you, antivirus and security monitoring, backup verification, priority remote and on-site support, network health checks, quarterly reviews and recommendations, and one point of contact — Jerry — who actually knows your business. No call centers, no ticket queues.

How much does managed IT cost for a small business in Winchester VA?

Plans start at $35/month per device on a 12-month plan, then it converts to month-to-month. Add managed antivirus at $69/year per computer or $49/year per phone or tablet. Project work and one-off repairs are billed at $95/hour for managed clients (vs. $125/hour standard).

How is managed IT different from break/fix?

Break/fix is reactive — you call when something breaks, you pay per hour, you have no predictable IT cost. Managed IT is proactive — Jerry monitors your systems, installs updates, runs security checks, and catches problems before they become emergencies. Most issues get handled before you notice them, and you have a predictable monthly fee.

Do you require long-term contracts?

The managed IT plan is a 12-month agreement, then it converts to month-to-month. Onboarding a new client takes real engineering hours up front (network audit, agent deployment, security baseline, backup setup), and a 12-month commitment is what lets me invest that time at the $35/device rate without marking it up. Most MSPs lock you into 1- to 3-year deals; one year is the floor that works for everyone.

Can you support remote employees and distributed teams?

Yes. SKTS offers an equipment depot (Jerry ships pre-configured machines to your employees), server hosting at SKTS, secure VPN setup for remote access to the office, and cloud collaboration setup (OneDrive, Google Drive, SharePoint, Zoom, Teams). Built for distributed teams with no central office.

What if I already have someone handling IT — can we add managed services on top?

Absolutely. Jerry often works alongside an internal employee or existing vendor to handle monitoring, patching, security, and after-hours coverage. He'll coordinate without stepping on toes. Call 540.303.2410 to talk through your current setup.

Do you handle Microsoft 365 and Google Workspace?

Yes. SKTS sets up, manages, and supports both Microsoft 365 and Google Workspace — including email migration, shared drives, calendar sharing, OneDrive/SharePoint, and security policies. Jerry also helps non-profits and qualifying organizations access discounted or free tiers.

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