What Is the Best Business Insurance for Small Companies with a Few Employees?

Question

We’re currently insured through Simply Business for our landscaping and property maintenance company, and I wanted to open up a discussion with other contractors here.
I’m curious how others are structuring their coverage and what the current market looks like for small crews.
For those in landscaping, lawn care, pressure washing, or similar service industries:

Who are you insured with (Simply Business, NEXT, Hiscox, State Farm, local agents, etc.)
What coverage do you carry (General Liability, Commercial Auto, Workers’ Comp, Tools &amp;
Equipment, Umbrella, etc.)?
What are you roughly paying monthly or annually?
How has your experience been with claims, renewals, or customer service?
Any providers you’ve found especially good or worth avoiding?

Just trying to benchmark where we’re at and see how other small crews (1–5 employees) are handling insurance as they grow.
Appreciate any insight—this kind of real-world info is incredibly helpful for newer companies like ours.
Sassenach Landscape &amp; Maintenance LLC

marepair2025 · Answer

I do handyman work and I’m insured through American family. It’s about $1700 a year for general liability that covers some trailers. We use our personal vehicles and they are insured personal currently. We don’t use work comp as we are just me and my brother as owners with no employees so work comp is not needed. We haven’t had any claims yet thankfully. And we haven’t shopped around much. We are open to suggestions if someone has found a nice insurance&nbsp;

bhhman · Answer

In the Nashville area, I use Darryl Price for my insurance needs. I’ve been quite pleased overall.&nbsp;

freshscape · Answer

Acuity Insurance is good and reasonable at your size.

robbale366 · Answer

We have acuity general liability with the option for a named insured as a handyman and its a little over 800 for a year or 1000 if you do the two pay option every 6months.

So far seems pleasant not that we've had to use them

teig_cl8ne · Answer

As a business owner who had to deal with a lot of hoops to jump through for cleaning a apartment complex it was nice to have a actual insurance agent who specialize in different insurances to get you the best deal. It was more convenient for me to have them do all the paperwork because I didn't have to come back and forth with the apartment complex. They dealt with all the paperwork and I just needed to focus on my work. It was a breath of fresh air especially. They're also good at letting you know as a business what you should and shouldn't have. For instance I have general liability I do not have workers comp but I can have workers comp because of the fact that it's me which I did not know until recently that it's a good idea. If you get hurt on the job and that's your only means of income it makes sense. It's a struggle I know, but find someone local that can walk you through step by step and knows your state laws.

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What Is the Best Business Insurance for Small Companies with a Few Employees?

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