The gutter company's guide to seasonal follow-up

Last October you cleaned gutters for 60 different homes across Waukesha County. This October, most of those homeowners have forgotten your name. They will just Google "gutter cleaning near me" and call whoever shows up first. That is a lot of repeat business walking away for no reason at all.

Why gutter work is built for repeat business

Gutters need cleaning on a schedule. Most homes need it spring and fall. Some need it just once a year, depending on the trees around the house. That means every past customer is a near sure repeat job. You just need to reach out before they think to search for someone new.

This is not like a one-time job such as a roof replacement. You already know these customers need the same service again on a set timeline. The only thing missing is a reminder.

Building the list

You probably have names and numbers from past jobs. They might sit in a spreadsheet, a Notes app, or old text threads. Pull them into one simple list. Use three columns: name, phone number, and last service date.

Do not overthink this. Even a rough list built from scrolling old texts beats no list at all. You only build it once. After that, you just add new customers as you go.

The fall message

Send this two to three weeks before leaves are mostly down in your area. In southeast Wisconsin that is usually mid to late October:

"Hey, this is [Name] with [Company]. Leaves are starting to come down and it's about that time for gutter cleaning. Want me to get you on the schedule for this month?"

It is simple and direct. It reminds them without asking them to remember on their own.

The spring message

Spring cleanings catch what winter left behind. That includes ice buildup, loose fasteners, or debris missed in the fall rush. Send this in late March or early April, once the ground has thawed:

"Hey, this is [Name] with [Company]. Spring thaw's here, good time to check your gutters for anything winter left behind. Want me to swing by and take a look?"

Why texting beats a mailer

A printed mailer costs money to design and print. Most go straight in the trash unread. A text costs you nothing but a few minutes to send. It lands right on a phone people check dozens of times a day. For a seasonal reminder, a text beats paper on cost and on response rate.

What kind of response to expect

Say you send this to 60 past customers each fall. A realistic response rate lands around 20 to 30 percent booking that same week. More trickle in over the next month. That is 12 to 18 jobs from a message that took maybe 20 minutes to send, with zero ad spend.

Timing it around Wisconsin weather

Do not send the fall message too early. If leaves are still mostly on the trees, people read it, agree in their head, and then forget. Wait until leaves are visibly coming down. The timing will feel real without you saying "urgent" at all.

The same logic holds in spring. Send it before the thaw and gutters might still have ice in them. A homeowner might say "let's wait a few weeks."

Keeping the list current

Add every new gutter customer to the list right away. Note the season you did the work. Your list grows every year with no extra effort. Two years from now you will have hundreds of past customers, each one getting a well-timed reminder instead of forgetting about you.

If writing these seasonal messages feels like one more thing on your plate, check out 30 Claude prompts built for contractors. It is a ready-made set for this kind of contractor follow-up.