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Answer 'how much will this cost?' messages with one saved reply that asks the right questions, then let estimate follow-ups run

who 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)

What it does

He had AI set up auto-responses: when someone messages asking what a job will cost, he pushes a button on his phone and a predetermined, professional reply goes out that asks a lot of detailed questions. He also has a follow-up system, like a CRM, that follows up with the customer repeatedly after an estimate is sent "until they buy or die": until they say yes or ask him to stop. The tools aren't named.

Tool cost

ChatGPT Free $0; Go $8/mo; Plus $20/mo · Claude $17/mo billed annually ($20 monthly); free plan available (his auto-reply and follow-up tools aren't named; any texting or CRM tool you already use can hold the saved replies)

Setup

Easy · or we do it from $149/mo

Tools

Varies

The problem

Many messages are price shoppers collecting three estimates, and driving out to every one wastes time and gas on jobs he has little chance of getting.

What happened

He says the replies help weed out tire kickers, so he wastes less time on jobs he wasn't likely to get, and that serious customers see a company that has its stuff together. No figures are given. Self-reported.

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

  1. What Rave Renovation does: one tap sends a saved, professional reply to 'how much?' messages that asks the questions he needs before driving out, and a follow-up system keeps checking in after each estimate until the customer decides or asks him to stop.
  2. Use the prompt below in ChatGPT or Claude to write the saved reply and three follow-ups, then save them as quick replies or templates in your phone, Facebook page or CRM.
  3. Time the follow-ups (for example day 2, day 7 and day 21 after the estimate) and stop them the moment the customer answers or says no.
  4. Answer real questions yourself: the saved reply gathers information, it doesn't quote prices or diagnose leaks.

Copy-paste prompt

Write a saved reply for {COMPANY NAME}, a roofing and renovation company in {AREA}, to send when someone messages 'how much will this cost?'. It should thank them, say we give written estimates after seeing the job, and ask 4 to 6 short questions: address, what's going on, how old the roof is, whether it's leaking now, insurance claim or not, and best time to visit. Keep it under 90 words. Then write three short estimate follow-ups for day 2, day 7 and day 21 that end with an easy way to say yes or 'no thanks'.
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