We delivered an AI Service Plan Manager for an eleven-person Ladson seamless gutter company whose twice-a-year cleaning plan ran on a calendar the trees ignored -- one that learns from every crew photo which canopy hangs over each of 1,860 houses and books each in its own window, chases every declined renewal on its own, and pulls lapsed plans off the route before a truck cleans them for free.

He bought his first gutter machine in 2014 for $11,000 -- a used five-inch roll former bolted to a trailer -- and parked it in his mother's driveway off Ladson Road. Twelve years later the shop sits a mile from the Exchange Park fairgrounds: three install crews, two cleaning trucks, two people in the office, eleven in all. The installs pay the bills. The thing he is proudest of is the cleaning plan: $219 a year, two visits, gutters and downspouts flushed.

He sells about a hundred of them every fall from a booth at the Coastal Carolina Fair, and 1,860 houses from Goose Creek to Summerville were on it by January. The plan had one flaw, and it was the calendar. The office booked every house in two waves, spring and fall, zip code by zip code, because that was the only way two people could keep 1,860 addresses straight. The trees in this part of the Lowcountry do not keep that calendar.

Loblolly pines drop their needles in the fall. Live oaks are evergreen and shed almost all at once in March. Sweetgums and water oaks let go in late November and keep going. A house in Crowfield under three live oaks, cleaned on schedule in October, was overflowing by the first of April.

A house in Wescott under pines, cleaned in April, was spilling over the front door by Thanksgiving. Last spring the trucks made 236 free return trips to gutters that had been cleaned within sixty days. Separately, 138 plans lapsed on declined cards that nobody chased, and because the route sheet did not know, the crews cleaned 61 of those houses anyway, for nothing. We delivered an AI Service Plan Manager that runs on the laptop in his office, under his own account, and gives every house its own calendar.

It wakes on four things: a crew finishing a visit and uploading its before-and-after photos to the job software, a renewal charge posting or declining, the first of each month, and any night the rain gauge at the shop reads more than two inches. From each set of photos it records what hangs over that roof -- pine, live oak, water oak, sweetgum, open sky -- and how full the gutters were when the crew arrived. After two visits it knows when that particular house fills, and it moves that house's two windows to match. On the first of the month it books every house whose window opens in the next four weeks, texts each homeowner a date, and routes the two trucks neighborhood by neighborhood.

Every new plan sold at the fair gets one question in its welcome text: what trees hang over your roof? On renewal day it charges the card on file. If the card declines, it sends a link to update it and tries once more three days later. If the plan is still unpaid, the house comes off the route before any truck can clean it for free.

The boundary is written down. It books, moves, renews at the agreed price, and sends a crew to reseal a seam that is under the company's own workmanship warranty, all on its own. It never sells. When a photo shows a crushed downspout, rotten fascia or a run that should be replaced, the photo and one line go into his morning report, and the quote is his.

It never charges anything but the plan price, never tries a card a third time, and never cancels a plan; a lapsed plan is paused, and only he can end one. The third weekend in March, the live oaks let go in a dry, windy week, and then on Saturday night it rained two and a half inches. He had turned his phone off for the weekend for the first time in nine years, at a cabin on Lake Marion. By Sunday morning, 47 homeowners had texted the office with water coming over the front of the house.

The AI matched each one against its last visit. Thirty-four were plan customers inside their guarantee, and it put them on Monday and Tuesday routes and told each one when. The other thirteen were not on the plan; it offered them the published one-time cleaning price and booked nine. He read about all of it Sunday night, on the drive home.

This spring the trucks made 31 free return trips, down from 236. Renewals went from 91 percent to 97. No house on a lapsed plan has been cleaned for free since February. The woman who used to spend March and October on the phone rescheduling now spends them calling the houses the photos flagged, and she sold more gutter guards in April than the company sold all of last year.

"For ten years I thought the job was cleaning gutters," he said. "It turns out the job was remembering eighteen hundred backyards. I don't have to remember any of them now."