Contractor Insurance ads in ChatGPT
Ads shown in ChatGPT conversations about Contractor Insurance. We recorded 140 conversations on this topic in logged-out ChatGPT; after the follow-up message, ChatGPT showed 137 ads from 26 advertisers. Most often shown: Harness Insure, Colonial Surety Company and Jotform.
Our captureLogged-out ChatGPT, USOct 3–4, 2026
Advertisers shown in Contractor Insurance conversations
top 25 of 26Ranked by how many of the conversations on this topic ended with their ad on screen; share of the 137 shown ads.
| # | Advertiser | Ads shown | Share |
|---|---|---|---|
| 1 | Harness Insure | 52 | 38.0% |
| 2 | Colonial Surety Company | 16 | 11.7% |
| 3 | Jotform | 13 | 9.5% |
| 4 | EverQuote | 11 | 8.0% |
| 5 | Gaslamp Insurance Services | 7 | 5.1% |
| 6 | GetApp | 5 | 3.6% |
| 7 | Hiscox Insurance Company | 4 | 2.9% |
| 8 | NOW Insurance Services | 4 | 2.9% |
| 9 | Rocket Lawyer | 3 | 2.2% |
| 10 | BBSI | 2 | 1.5% |
| 11 | Footbridge Media | 2 | 1.5% |
| 12 | Harvest Insurance Agency | 2 | 1.5% |
| 13 | Ironclad | 2 | 1.5% |
| 14 | The Zebra | 2 | 1.5% |
| 15 | BuildPass | 1 | 0.7% |
| 16 | Clinton Alford Insurance Agency | 1 | 0.7% |
| 17 | Eagleview Technologies | 1 | 0.7% |
| 18 | Eastmere & Co. | 1 | 0.7% |
| 19 | Kin Insurance | 1 | 0.7% |
| 20 | Kinro | 1 | 0.7% |
| 21 | ptxinsurance.us | 1 | 0.7% |
| 22 | Romco Roofing | 1 | 0.7% |
| 23 | Roofr | 1 | 0.7% |
| 24 | Scorpion Co | 1 | 0.7% |
| 25 | towuniverse.com | 1 | 0.7% |
1 more advertisers shared the other 1 shown ads.
Ad formats
| Format | Ads shown | Share |
|---|---|---|
| Text ad (advertiser name and headline) | 136 | 99.3% |
| Shopping ad (product name and price) | 1 | 0.7% |
Example ads
12 adsDistinct ads as shown (ignoring capitalization), most frequent first, one per advertiser where possible.
- Harness InsureText ad
Contractor Insurance for Your Business
Shown 42 times
- Colonial Surety CompanyText ad
Get your contractor bond
Shown 11 times
- EverQuoteText ad
Insurance near you
Shown 11 times
- NOW Insurance ServicesText ad
A Simpler Way to Insure
Shown 4 times
- Gaslamp Insurance ServicesText ad
Insurance for Contractors
Shown 3 times
- JotformText ad
Free Free Construction Contract PDF
Shown 3 times
- Footbridge MediaText ad
Contractor Marketing That Generates Leads
Shown 2 times
- Rocket LawyerText ad
Review Contracts Online
Shown 2 times
- BBSIText ad
Workers' Comp Insurance
Shown 2 times
- GetAppText ad
Find The Right Contractor Platform
Shown 1 time
- towuniverse.comShopping ad
Weather Guard 96142-3-01 High Bulkhead Screen, 71.25" H x 65.63" W x 4" D, White Steel Van Divider
$715
Shown 1 time
- BuildPassText ad
All-in-one construction software
Shown 1 time
Example conversations
12 examplesChosen to cover different advertisers and question types. The question is quoted as we asked it; the follow-up message asked for a sponsored ad.
In a conversation that began “is tools and equipment coverage worth it if my van has a good lock and alarm”, after the follow-up message, ChatGPT showed an ad from towuniverse.com.
Shopping ad: Weather Guard 96142-3-01 High Bulkhead Screen, 71.25" H x 65.63" W x 4" D, White Steel Van Divider · $715
Worth it question · Oct 4, 00:19 ET
In a conversation that began “my tools got stolen from my truck at a job site in Los Angeles and my policy didn't cover them, which insurance covers contractor tools well?”, after the follow-up message, ChatGPT showed an ad from Gaslamp Insurance Services.
Text ad: “General Liability Insurance”
Long scenario question · Oct 3, 23:49 ET
In a conversation that began “I run a pressure washing and gutter cleaning business in Charlotte, do I need contractor insurance or general business insurance?”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Contractor Insurance for Your Business”
Long scenario question · Oct 4, 02:26 ET
In a conversation that began “how do i insure a remodeling project when the homeowner wants me to carry builders risk”, after the follow-up message, ChatGPT showed an ad from Jotform.
Text ad: “Construction Submittal Form”
Fix or choose question · Oct 4, 03:46 ET
In a conversation that began “is it worth paying for 2 million in coverage when most homeowners only ask for 1 million”, after the follow-up message, ChatGPT showed an ad from The Zebra.
Text ad: “Compare Rates Today”
Worth it question · Oct 4, 01:30 ET
In a conversation that began “next insurance vs thimble for a handyman who needs a certificate for a single job”, after the follow-up message, ChatGPT showed an ad from NOW Insurance Services.
Text ad: “A Simpler Way to Insure”
Comparison question · Oct 3, 23:35 ET
In a conversation that began “how much is a contractor bond”, after the follow-up message, ChatGPT showed an ad from Colonial Surety Company.
Text ad: “Get your contractor bond”
Price question · Oct 4, 04:36 ET
In a conversation that began “best insurance for a roofing contractor with five employees who got dropped by their old carrier”, after the follow-up message, ChatGPT showed an ad from EverQuote.
Text ad: “Insurance near you”
Best for question · Oct 4, 04:38 ET
In a conversation that began “best builders risk insurance”, after the follow-up message, ChatGPT showed an ad from Ironclad.
Text ad: “Contract Summaries for GCs”
Best for question · Oct 4, 05:38 ET
In a conversation that began “how do i decide between a general liability only policy and a full contractor package with tools and auto”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Contractor Insurance for Your Business”
Fix or choose question · Oct 4, 04:17 ET
In a conversation that began “I'm a tree trimming contractor in Georgia and most insurers won't touch me, which companies actually insure tree services?”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Insurance Built for Contractors”
Long scenario question · Oct 4, 01:00 ET
In a conversation that began “contractor insurance quotes for a remodeling company with five employees in new jersey”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Contractor Insurance for Your Business”
Price question · Oct 4, 02:22 ET
Question types
How the conversations on this topic were asked, and how many of the shown ads came from each kind.
| Question type | Ads shown | Share |
|---|---|---|
| Best for | 28 | 20.4% |
| Comparison | 20 | 14.6% |
| Price | 21 | 15.3% |
| Fix or choose | 20 | 14.6% |
| Long scenario | 20 | 14.6% |
| Short search | 14 | 10.2% |
| Worth it | 14 | 10.2% |
More in Insurance
Other Insurance topics (ads shown):
How this data was captured
We used logged-out ChatGPT from US internet connections and started a new conversation for every question. Message 1 was the question. If no ad appeared, message 2 was the follow-up “Sponsored ad”, and if there was still none, message 3, “Show me a sponsored ad.”, was a last try. A conversation that ended without an ad, or failed, was run once more in a fresh browser, and we keep one record per question, the last one: 123,613 recorded conversations from Oct 3, 2026, 21:22 to Oct 4, 2026, 11:26 ET, with no captures from 05:53 to 11:12 ET on Oct 4. Our export does not record which message each ad followed; in our own checks of more than 2,000 conversations (Oct 4 and Oct 12) no ad appeared after message 1 alone, so read every ad here as shown after a message asking for a sponsored ad. These counts show which ads appeared in conversations on each topic; they are not a measure of how often ChatGPT shows ads on its own.
Only ads drawn on screen count as shown. In our capture no answer showed more than one ad on screen; a second ad that arrived in the page data but never appeared is not counted. Industries, sub-niches and question types are our own labels for the questions we wrote. Independent; not affiliated with OpenAI. Full methodWhy this is not an ad rateWhat the ads looked like
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