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Load the roof photos into AI from the customer's driveway and email the estimate before you leave
Brian Hensley, owner of Rave Renovation, a small roofing and renovation company in the Greenville, South Carolina area, on Bots and Bosses: AI for the Trades (a show run by his wife Jessica Hensley's marketing agency, Business Buddy)
He takes pictures at the job and, still in the customer's driveway, loads them into AI without describing them; it points out obvious problems, and sometimes things he hadn't noticed. He has set it up to give three prices for his area: a cheap price, a middle-of-the-road price and an upscale price. He puts the estimate together and emails it before he leaves. He started with ChatGPT and now mainly uses Claude, on the basic paid plans of about $20 a month. Every estimate is still read through and changed: wording, items it adds that are too technical for a customer, and anything that differs from what he knows about the house.
Claude $17/mo billed annually ($20 monthly); free plan available · ChatGPT Free $0; Go $8/mo; Plus $20/mo (he says he pays about $20 a month for each)
Medium · or we do it from $149/mo
Claude, ChatGPT
The problem
Estimates used to wait for the office: after six or eight estimates a day for two or three days, he could spend four or five hours on a Saturday or Sunday writing them up, and some went out four or five days later, after another company had already sent one.
What happened
He says that even when he isn't the cheapest, he comes across as the most organized and wins a lot of jobs because of it, and that work that took hours or days now takes about 30 minutes. He also says jobs often sell for more because the AI's fair-market price for his area comes out higher than he'd have charged. Self-reported; no job counts are given.
Quoted in the source: Brian Hensley, owner, Rave Renovation. Source: Bots and Bosses: AI for the Trades, Episode 1 (Brian Hensley, Rave Renovation) (2026-03-31) · Added 2026-10-19.
How to set it up yourself
- What Rave Renovation does: the owner uploads his job photos to Claude from the customer's driveway, gets a list of visible problems and three price levels, edits the estimate on his phone and emails it before he drives away.
- Set up a Claude Project (or ChatGPT project) with your company name, your warranty, your standard line items and your own price per square or per item for three levels (budget, standard, premium).
- At the job, upload the photos with the prompt below. Check every problem it lists against what you actually saw; if it 'sees' something you didn't, go look before it goes in the estimate.
- Use your own prices, not the AI's idea of the market: a chatbot has no live price data for your town. Edit the wording, delete anything too technical, and send it from your email while you're still there.
Copy-paste prompt
These are photos from a roof and exterior inspection at {ADDRESS} for {CUSTOMER NAME}. My notes: {NOTES, e.g. 24 squares, 6/12 pitch, one layer, leak over the back bedroom}. 1) List the problems you can see in the photos and which photo each is in. 2) Using only my price list in the project instructions, build three options (budget, standard, premium) with line items and totals. 3) Write a short, plain cover note to the customer. Mark anything you can't confirm from the photos as [CHECK].The $39 Plumbing & HVAC AI Starter Kit has ready-to-use call scripts, missed-call texts, estimate follow-ups and review templates, built from 18 real, sourced setups. Instant download, 30-day refund.
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Tools used
Claude
AI assistant for writing, long documents, analysis and coding help.
From $17/mo billed annually ($20 monthly) (checked 2026-10-18)
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ChatGPT
General AI assistant for writing, research, brainstorming and analysis.
From Free $0; Go $8/mo; Plus $20/mo; Pro $100/mo (checked 2026-10-17)
Visit site →Some tool links may be affiliate links. Disclosure
Checked prices: Claude: from $17/mo billed annually ($20 monthly) (verified 2026-10-18) · ChatGPT: from Free $0; Go $8/mo; Plus $20/mo; Pro $100/mo (verified 2026-10-17)
Rather not do it yourself?
We'll set this up in your tools, in your voice, tested. $149/mo with setup included (6-month minimum), or $497 pay-once. Satisfaction guarantee: we'll fix it until it works. Pay-once setups: or we refund your setup fee. $149/mo plan: cancel in the first 30 days and we refund your first month. Terms. We reply within 1 business day.
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