Woolf IT Solutions

IT support · Polk County · the I-4 corridor

The IT department for businesses that can't afford downtime.

IT Support in Winter Haven, Lakeland, and Polk County

Proactive IT, security, and compliance for offices of 1 to 50 people in Polk County and along I-4, run by one owner who answers the phone.

  • Insured
  • Microsoft partner program
  • 24/7 monitoring by human analysts

Lake country, Central Florida

Kevin Woolf, owner of Woolf IT Solutions

The person who answers

Hi, I am Kevin Woolf. You deal with me.

I own Woolf IT Solutions and I do the work. There is no tier one, no ticket routing, and nobody reading your account for the first time while you explain it again. You call one number and reach the person who fixes it.

1 to 50

The size of business we build for

24/7

Monitoring and alerting by a security operations center staffed by human analysts

100%

Your accounts, domain, and data stay in your name

Where it usually starts

Sound familiar?

If one of these four sentences sounds like your week, start there. Each one has a clear way forward.

“Our IT person just left.”

We take over cleanly. I inventory the systems and access first, secure the accounts, and plan each change with your team, with a fallback for the risky steps.

How the takeover works

“We got a compliance letter.”

HIPAA, IRS, FTC: we turn the letter into a checklist, and the checklist into documentation you can hand back.

Compliance for regulated offices

“Things keep breaking, and nobody calls back.”

You call one number and reach the person who does the work, and the recurring problems get fixed for good.

How we compare

“We have never had real IT.”

That is normal at your size. We start with a plain-English look at what you have, not a sales pitch.

Start with the assessment

Who we serve

Three kinds of offices. Three very specific jobs.

Every client gets the full plan. These three also get the exact piece of paper their work depends on.

HIPAA Security Risk Analysis

Healthcare, Medical & Dental

Patient data, practice software, and a front desk that cannot wait on technology.

HIPAA requires a Security Risk Analysis. We perform it, fix what it finds, and sign the Business Associate Agreement.

Medical and dental IT support

IRS + FTC WISP

Professional & Small Office

Accountants, attorneys, and agencies that live in email, documents, and the cloud.

The IRS and FTC require tax preparers to keep a written security plan. We write yours and run the controls behind it.

Get your WISP written

Jobsite Uptime

Trades & Construction

Crews in the field, change orders flying, and devices that take a beating.

The office stays up, the jobsite is in your pocket, and the help desk calls come to us.

Keep the crews moving

Managed IT support and IT services in Polk County and the I-4 corridor

Six disciplines, one monthly plan, one person accountable for all of it. Built on Microsoft 365.

Managed IT Support

Proactive monitoring, patching, and device lifecycle management, plus a real person to call. We keep the lights on so you can run the business.

Cybersecurity

Endpoint protection, multi-factor authentication, email filtering, and security awareness. Layered defense sized for a small business.

Compliance & HIPAA

Security controls, written policies, and documentation for regulated work. A practical fit for medical, dental, and other compliance-minded offices.

Backup & Disaster Recovery

Automated, tested backups of the data your business cannot lose, with a real recovery plan for when hardware fails or ransomware hits.

Virtual CIO & IT Strategy

Technology budgeting, roadmap planning, and vendor management. We act as your outsourced IT leadership, aligned to where the business is headed.

IT Projects & Migrations

New office, server replacement, Microsoft 365 move, or phone system. Scoped clearly, executed cleanly, finished on schedule.

Finished work

When the software can't do it, I build it.

Three recent jobs for local offices. Real figures, no names.

Saved a $17k camera

A replacement was priced at $17k to $24k. Instead, custom software got the old camera working again.

Software I built

A software company went under. I kept the imaging working.

A medical practice's imaging camera ran on software from two companies that had both gone out of business, and its license could not move to a new computer. In daily use since August 17. No new camera needed.

No monthly add-on

A custom QuickBooks estimate app instead of a $30 to $60 a month subscription.

Software I built

Estimates QuickBooks said it couldn't make. So I built it.

A contractor wanted its logo and two industry award badges on every estimate. QuickBooks Online allows neither extra images nor custom templates. Asked for on September 15. Delivered September 22.

Files anywhere, backed up daily

Moved off the office server into Microsoft 365. Now the files open on any work computer and are backed up every day.

Owning your systems

Off the office server and into the cloud

A six-person contractor kept its files on a server in the office. I moved the company's files into Microsoft 365 and switched every computer over. Files open from anywhere, and the old server sits unused.

The difference

Most providers sell you tickets and hourly bills. We act as your IT department.

Who answers

A typical IT shop: A rotating queue and an offshore call center

Woolf IT: One local owner who already knows your systems

Who fixes it

A typical IT shop: Tier 1 reads a script, escalates, and you wait

Woolf IT: The person who answers is the person who fixes it

Service model

A typical IT shop: Reactive break-fix that bills by the hour

Woolf IT: Proactive managed services on a flat monthly plan

Pricing

A typical IT shop: Vague contracts and surprise line items

Woolf IT: $125 per person per month, published right here, in plain English

Your accounts

A typical IT shop: Your accounts and domain end up under their master account

Woolf IT: Your accounts, domain, and data stay in your name, always

Local presence

A typical IT shop: A name on a national franchise list

Woolf IT: Based in Winter Haven, accountable to Polk County and the I-4 corridor

Pricing

The price, published.

Most IT companies make you book a call to hear a price. This is ours, for everything in the managed plan. Microsoft 365 licenses and the password manager are separate lines, and your plan page shows the full monthly total before anything starts.

$125

per person, per month

Every line is on the plan page you approve before anything starts.

Book a free IT assessment
  • Monitoring, patching and updates on every computer
  • Microsoft Defender configured and watched: the automatic layer
  • Huntress, the people layer: a human-staffed security operations center watching around the clock
  • Security awareness training and phishing practice for your team
  • Daily cloud backup of company files, restored on purpose
  • Help desk with the owner, the person who already knows your setup
  • Written security policies, plus the HIPAA Security Risk Analysis or a tax firm's WISP, kept current
  • A technology plan a year ahead, so nothing surprises you

Billed separately, at cost or at the maker's own price

  • Microsoft 365 licenses, at Microsoft's own price
  • Password manager with dark web monitoring, one small per-person line
  • Computers and equipment, passed through at cost
  • Projects such as a move, a migration or a new phone system, quoted up front
The Winter Haven chain of lakes seen from the air, with waterfront neighbourhoods along the shoreline

Small offices get hit because they are reachable, not because they were chosen.

What we do about it

The chain of lakes from above

A clear path from chaos to calm

  1. Assess

    We document what you have: devices, accounts, security gaps, and what keeps you up at night.

  2. Secure

    We fix the urgent gaps first, planned around your business so your team keeps working.

  3. Manage

    You move onto the monthly plan: monitoring, patching, backup, security, and a plan a year ahead.

Switching feels risky. It should not be.

The handoff from your old provider is our job, not yours. We collect the credentials and the documentation, and we make the awkward phone call.

A great blue heron standing still in the shallows of Lake Howard in Winter Haven

The real product is the quiet month.

Backups restored on purpose, patches applied on a schedule, alerts read by people. When nothing needs your attention, everything is working.

Great blue heron, Lake Howard, Winter Haven

Straight answers, no jargon

$125 per person per month for the whole managed plan. Microsoft 365 licenses and the password manager are separate per-person lines at their own price, and computers are passed through at cost. Every line is on the plan page you approve before anything starts.

You call one number and reach the owner, not a queue. The person who answers is the person who fixes it, and urgent issues go to the front of the line. You are never waiting on a national ticket system to route you.

Your protection doesn't wait on my calendar. Huntress's security team watches your computers and accounts around the clock, and monitoring, patching and backups run on schedule whether I'm at my desk or not. Everything is documented, with the passwords in your business's own vault, so nothing lives only in my head. If I'll be away, you'll hear about it ahead of time.

No multi-year handcuffs. We earn your business month over month, and your accounts, domain, and data stay in your name, so you can leave any time and take everything with you.

Yes. For medical, dental, and other regulated offices we build security controls and keep the written policies and documentation that compliance and insurance reviews ask for. The HIPAA Security Risk Analysis and a tax firm's WISP are part of the managed plan, not an extra charge.

We audit and document what you have first, keep what is working, and improve the rest on a schedule that fits your business, with a fallback planned for the risky steps. No rip and replace.

Ongoing managed-service plans are billed on the agreed monthly schedule. Project and hardware work is invoiced against your approved quote. Everything is scoped up front, with no surprise charges.

We are local to Winter Haven, Lakeland, Polk County, Central Florida, Haines City, Davenport, Bartow, Auburndale, Kissimmee, Plant City, and the I-4 corridor. If you are a small business in the area, we can help.

Yes, where it saves your office real time. When the software you already pay for cannot do what you need, I build the missing piece: a QuickBooks estimate template, camera software after the vendor folded, a dashboard that pulls your numbers together. AI tools get the same treatment: set up with guardrails so your team gets the value without putting client data at risk. The case studies show what that looks like.

Kevin Woolf, owner of Woolf IT Solutions

Kevin Woolf, Owner

The person who answers your call.

A note from Kevin

Why I started Woolf IT

I started Woolf IT on a simple idea: small businesses deserve IT as reliable as the work they do. I live and work in Winter Haven, same as the companies I look after.

I run the same systems I set up for clients. When I recommend something, it is because I depend on it myself.

One accountable person who knows your business and plans a year ahead. If that is the IT you have been looking for, call me. I answer.

Kevin Woolf · Owner, Woolf IT Solutions LLC

A wooden dock reaching into Central Florida water at sunset

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Sunset on the water