Gutter cleaning services insurance checklist: what a gutter cleaning company should carry

The gutter cleaning company insurance checklist

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Gutter cleaning services usually carry general liability, workers' compensation and commercial auto. Gutter cleaning companies do simple work in a dangerous place: ladders against the eaves of two-storey houses, often in autumn weather, with seasonal help hired fast. The property manager and the permit office ask for proof of each. The checklist below says what every item does, who requires it and how to check it on the policies you already have.

Reviewed by Michael LaBarbera, Licensed property & casualty agent, Provident Financial Group · Reviewed Oct 12, 2026 Updated Oct 14, 2026

Who asks a gutter cleaning company for what

Who	What they usually want to see
Property managers & HOAs	General liability with the manager and owner as additional insureds, and workers' compensation
Cities, counties & permits	General liability, auto and workers' compensation at the limits in the permit or contract
Banks, lenders & SBA loans	Property or auto physical damage with the lender as loss payee, and liability proof at closing and every renewal

Each of them wants a certificate, and most want it again at every renewal. A live certificate link from the wallet shows today's coverage to every holder and tells them when it changes.

How to check what you already have

General liability declarations page. Three liability numbers matter: each occurrence, general aggregate and the products–completed operations aggregate. Then the forms list: blanket additional insured, waiver of subrogation and primary and non-contributory wording satisfy every contract; scheduled forms satisfy one.
Workers' compensation information page. Item 3.A must list every state you work in, item 4 must carry the right class codes, and the employers' liability limits should meet what contracts ask. Check that the estimated payroll is close to this year's.
Auto schedule. Every vehicle listed with the right garaging address and use; symbols that include hired and non-owned auto; physical damage with the lender as loss payee where the vehicle is financed.
Equipment schedule. Owned items scheduled above the per-item threshold, a blanket limit for small tools, leased or rented equipment included, and the valuation (replacement cost or actual cash value).
Hired and non-owned auto. Look for the symbols 8 and 9 or an endorsement by that name on the auto or general liability policy; without it, staff in their own cars are uninsured on company business.
Employment practices declarations. Limit and retention, third-party coverage for claims by customers, and whether wage-and-hour claims carry any defence sublimit.

What usually goes wrong for gutter cleaning services

A fall from a ladder by a seasonal helper with no workers' compensation in place.
Ladder damage to siding, gutters and landscaping, and a dispute about whether it was already there.
Damage to the exact thing you are working on is excluded on most general liability forms; installation floaters and care, custody and control endorsements fill that hole.
Height exclusions on general liability policies written for ground-level work.
Theft from a locked truck overnight with no tools floater, or a per-item limit lower than the one tool that mattered.
A personal auto policy on a truck with the company name on the door.

What underwriters will ask a gutter cleaning company

Number of workers and when they are hired, maximum height worked, and whether the business also installs guards
Residential versus commercial split of the work
Whether any work is done above three stories or below grade
The maximum height you work at and how often
Fall-protection practices and training
Total value of hand and power tools kept on the trucks

Have the answers in the wallet before the renewal and the quote request fills itself in; CoverMatch sends one application to every eligible carrier and lines the quotes up against what you have.

Renewal timing

Audits at year end compare payroll, receipts and subcontractor costs with the estimate, so keep the wallet's size figures and the subcontractor certificates current. Start comparing sixty days before expiration, and ask for the limits the next contract will need rather than the ones the last one did.

Questions people actually ask

Is workers' compensation worth it for a two-person gutter company?

It is the policy that matters most. Falls from ladders are the whole exposure of the trade, the state requires the coverage from the first employee in most of the licensed states, and a single fall without it can end the business.

A homeowner says we dented their gutters. What covers it?

Damage to the gutters you were cleaning is property in your care and may be excluded; damage to the siding or garden is ordinary general liability. Photographs before and after every job settle most of these in minutes.

Does general liability cover damage to a customer's property while I work on it?

It covers damage to the rest of their property, not usually the part in your hands. Many forms exclude property in your care, custody or control, so a gutter cleaning company that handles valuable items or systems needs an endorsement or an installation floater. The policy explainer in the wallet flags the exclusion when it reads your policy.

Do I need workers' comp if my crew is small?

Most of the licensed states require it from the first employee, and general contractors require it from every sub whatever the size, because an uninsured sub's payroll is charged to their policy at audit. The state pages list each threshold with its source.

Are tools stolen from my truck covered?

Under a tools floater, yes, subject to the deductible and any per-item limit. Under the commercial auto policy, no: auto covers the vehicle, not what was in it.