Rebook Past Customers, and Last Year's Jobs Become Your Winter Paycheck

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The Winter Hole Nobody Plans For

From January to March the calls stop, according to dcbrock in a 2020 thread asking for winter advice. Another owner described the same hole.

"I try my best to have saved up through the season to make it through an always unexpected bad winter (4months)."

HIX, PressureWashingResource forum, Nov 2019

The winter threads we read are full of gutters, Christmas lights and side jobs. Nobody mentioned contacting last year's customers or pre-booking spring work.

Window cleaners, who live on repeat work, did talk about it. WDW wrote "I sent reminder cards in the spring and fall with a small coupon if scheduled before a certain date and that, more than anything, created repeats." Cinder brings an iPad to every job and, as he puts it, "at the end if the job I schedule the next cleaning." He says it "has greatly increased repeat business." Denver13 puts it as "I always leave a job with a job."

DeepC explained why a system beats good intentions.

"People rarely do what they say they need to do."

DeepC, Window Cleaning Resource forum, Oct 2018

"Call me next year" means you call them. Otherwise the next door hanger or Facebook ad gets the job.

The 12-Month Re-Service System

1. Book the next visit before you leaveAt the walk-around, when the customer is happiest with the job, offer to pencil in the same time next year. It's the cheapest booking you'll ever make.Job done → walk-around → "Want me to pencil you in for next May?"
2. Tag every jobRecord the service (house wash, roof, driveway, gutters), the date, the price and a short note such as "north side mildew heavy" or "declined gutter brightening." A tagged list sends the right reminder at the right time, and the note hands you next year's upsell.
3. Send the reminder at 11 monthsSend it a month before the anniversary, before someone else's flyer lands. Include this year's price and two dates.
4. In January, text every past customerOffer spring dates and give past customers first pick. Add a small incentive for booking by a deadline. The script below uses $25 off, but pick your own number. That's how April fills up while it's still cold.
5. Mail postcards to the ones who don't text backdcbrock wrote in the window cleaning thread, "We have also used handwritten postcards with great success." On PWR, Clean1 uses "send jim for automated postcard campaigns and thank yous," and KNBExteriors noted "You can set up auto email drip campaigns to keep your business in front of your customers."

What to Say on Site and by Text

Before I pack up: want me to pencil you in for the same time next year? I'll text you a week before to confirm, and you can move it or cancel, no problem.

Hi {first name}, it's {your name} with {company}. It's been almost a year since we washed your house{ and driveway}. Want to get on the schedule for {month}? Same job is {price} this year. I have {date 1} or {date 2} open.

Hi {first name}, {your name} from {company}. I'm building the spring schedule now, and past customers get first pick of dates before I open it up. Book by {Feb 28} and I'll take {$25} off. Reply with a week that works and I'll lock it in.

Text only people who've hired you, and stop the moment anyone asks. Quotes that never turned into jobs belong in the follow-up cadence, and more wording is in the script pack.

Raising Prices on Repeat Customers

Window cleaners split on this. Infinity wrote "In general we raise prices on current customers by 10% every 3 years." Pioneer_Services goes the other way with "I don't announce the price increase, I just raise the price," and says only "5-6 people in 10 years" ever commented. Either way, the new price goes in the 11-month text with no speech. If last year's price was a newbie price, fix it now instead of discounting your way back down.

What Your List Is Worth

List value = past customers × share who rebook × average ticket

Nobody publishes a reliable rebook rate for pressure washing, so we won't invent one. Swap in your own count and ticket, and try a few rebook rates.

Example only: 150 customers and a $350 ticket are placeholders, not industry figures. Use your own job history.

Even the low row lands in the months HIX was saving up for, and costs next to nothing beside new leads.

Do It by Hand, or Let Software Send It

A list of a hundred or two needs a spreadsheet sorted by service date, a calendar reminder at 11 months and a couple of evenings in January sending texts by hand. It works if you do it every year.

The window cleaner who wrote "I wish my scheduling software had automatic scheduling reminder emails for my residential clients" was describing the point where software starts to earn its fee.

As listed on QuoteIQ's and Jobber's pricing pages, October 2026. Postcards: owners name Send Jim; handwritten works too.

Start on QuoteIQ's entry plan with a recurring job set at every walk-around, and send the January text by hand. Move up to Elite when the list outgrows an evening of texting. QuoteIQ pricing has the plan details and the true cost by team size.

Sources

1. PressureWashingResource, "Need winter advice", Jun 18, 2020: dcbrock on January to March (paraphrased).
2. PressureWashingResource, "What do you guys do in the winter (climates that barely have snow)", Nov 1, 2019: HIX on saving for winter.
3. Window Cleaning Resource, "Getting clients to schedule", Oct 10, 2018: DeepC, WDW, dcbrock (postcards).
4. Window Cleaning Resource, "How should I remind customers to schedule", Mar 17, 2022: Cinder, Denver13.
5. PressureWashingResource, "What CRM does everyone use" (page 2), Apr 30, 2017: KNBExteriors, Clean1.
6. Window Cleaning Resource, "Do you increase your prices every year", Aug 26, 2014: Infinity, Pioneer_Services.
7. QuoteIQ, "Pricing", read Oct 12, 2026: recurring jobs, Pro automation, Elite mass campaigns.
8. Jobber, "Pricing", read Oct 12, 2026: Connect reminders, Marketing Suite add-on.