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ROOTED IN PLANT CITY & LAKELAND · SERVING CLIENTS ACROSS FLORIDA

Independent Insurance for Florida Businesses & Families

We're an independent agency with local roots and statewide reach, so we compare multiple carriers for your General Liability, BOP, Workers' Comp and Commercial Auto, plus your Home, Flood, Car, Boat, ATV and RV. You get one advisor who knows you by name.

What we insure

COVERAGE

Tell us what you need covered. We'll shop it across our carriers and walk you through the options.

Contractor in a hard hat inspecting new roof framing on a Florida job site

Business insurance

  • General Liability: Covers customer injuries, property damage and the claims that come with running a business.
  • BOP / Commercial Property: Liability and property in one package: building, equipment, inventory and business income.
  • Workers' Compensation: Protects your employees and your business when someone is hurt on the job.
  • Commercial Auto: Trucks, vans and cars used for work.
  • Commercial Umbrella: Extra liability limits over your GL, auto and employer's liability.
Light-blue Florida home with a front porch and palm trees

Personal insurance

  • Auto: Florida PIP, liability and the coverage you actually want, compared across carriers.
  • Home, Condo & Renters: Coverage built around your home, roof and Florida weather.
  • Boat & Watercraft: Boats, pontoons and jet skis, on the lake or offshore.
  • RV, ATV/UTV, Motorcycle & Golf Cart: Motorhomes, travel trailers, off-road machines, bikes and street-legal carts.
  • Personal Umbrella: An extra layer of liability over your auto, home and boat.
Couple reviewing papers with an advisor at a table

MEDICARE

Medicare Supplement & Part D

Turning 65 or reviewing your plan? We help you compare Medicare Supplement (Medigap) and Part D prescription drug plans.

Own a business and a home, car or boat? One advisor, one review, and bundle discounts where carriers offer them.

How it works

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Tell us what you need.

Answer a few questions online, or upload your current policy and skip most of the typing. Save your progress and finish later.

We shop it for you.

As an independent agency, we take your information to multiple carriers and compare coverage and price, so you don't have to fill out five applications.

You choose, with an advisor.

We walk you through the options, in person at our Lakeland office, by phone, video or email from anywhere in Florida, and help you pick what fits. Coverage starts only when it's confirmed in writing.

Café owner smiling behind her counter

Restaurants, bars & food trucks

Kitchen fires, slip-and-falls, liquor liability, spoilage after a power outage and staff injuries. We know what restaurant carriers ask about and help you get it right the first time.

Insurance for the businesses that keep Florida running

We insure small and mid-sized businesses of all kinds, and we spend a lot of our time with two of them.

Two builders reviewing plans inside a framed building

Contractors & trades

GL for contracts, Workers' Comp per Florida rules, tools coverage, and certificates for the GC.

INDUSTRIES WE KNOW

Small-business owner working inside her clothing boutique

Other small businesses

Retail, offices, salons, auto services and more: liability, property, workers' comp and commercial auto.

INSURANCE ACROSS FLORIDA

Local roots, statewide service

Our roots and our office are in Polk County, but we serve businesses and families all over Florida. Most of the process happens by phone, email, video and e-signature, so distance doesn't matter.

Map of Florida with a marker on Lakeland in Polk County

Home base: Lakeland, Polk County

WHY THE ROLLYSON GROUP

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“Do right by the client and the rest will take care of itself.”

— RAY H. “ROLLY” ROLLYSON JR.

We’re independent.

We work for you, not one insurance company, so we can compare options across carriers.

Local roots, statewide service.

Our team grew up in Plant City, Lakeland and the Tampa Bay area, and our office is on North Crystal Lake Drive in Lakeland. We serve clients across Florida.

You’ll know your advisor.

Business clients work one-on-one with JJ Niekro, who leads our commercial practice. Same advisor at quote time, at renewal and when you have a question. Personal clients get the same attention from our team.

We meet face to face.

Prefer to sit down and go over it? Come by the office. Prefer to do everything online? That works too.

Meet your advisors

Rhett Rollyson, Founder, The Rollyson Group

Rhett Rollyson

FOUNDER & PRINCIPAL

Lifelong Plant City resident and founder of The Rollyson Group. Rhett builds our carrier partnerships and keeps the agency true to its motto: do right by the client.

JJ Niekro, Head of Commercial Lines, The Rollyson Group

JJ Niekro

HEAD OF COMMERCIAL LINES

Former Florida Southern College and Atlanta Braves organization pitcher who now leads our commercial practice for businesses across Florida.

Skyler Barber, Chief Marketing Officer, The Rollyson Group

Skyler Barber

CHIEF MARKETING OFFICER

Skyler leads our brand, digital strategy and client outreach, and she makes sure Floridians know how to reach us.

Common questions

What does independent agency mean?

We're not tied to one insurance company. We're appointed with multiple carriers, so we can compare coverage and price for you and switch carriers at renewal if something better comes along.

What do I need to get a quote?

For personal insurance: names and dates of birth of drivers, your vehicles or property, and your current policy if you have one. For business insurance: what your business does, your revenue and payroll, number of employees, and your current policy and loss history. The easiest shortcut is to upload your current declarations page and we'll pull most of the details from it.

Does requesting a quote cost anything or commit me to anything?

No. A quote request is free and doesn't bind any coverage. Nothing changes until you choose a policy and it's confirmed in writing.

Can you insure my business and my personal stuff together?

Yes. Tell us about both when you start your quote. You'll have one review, and some carriers offer multi-policy discounts.

Do you only work with clients near Plant City and Lakeland?

No. Our roots and our office are in Polk County, but we serve businesses and families all over Florida. Most of the process happens by phone, email, video and e-signature, so distance doesn't matter.

I already have insurance. Can you still help?

Yes. Send us your current policy and renewal date. We'll compare it against other carriers before your renewal so you have time to decide.

Ready to see your options?

WHEREVER YOU ARE IN FLORIDA

Start online in a few minutes, or reach out and talk to a real person on our team, wherever you are in Florida.

Requesting a quote does not bind coverage.

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