Business Insurance ads in ChatGPT (Small Business Tools)
Ads shown in ChatGPT conversations about Business Insurance. We recorded 56 conversations on this topic in logged-out ChatGPT; after the follow-up message, ChatGPT showed 55 ads from 19 advertisers. Most often shown: Harness Insure, NOW Insurance Services and EverQuote.
Our captureLogged-out ChatGPT, USOct 3–4, 2026
Advertisers shown in Business Insurance conversations
19 advertisersRanked by how many of the conversations on this topic ended with their ad on screen; share of the 55 shown ads.
| # | Advertiser | Ads shown | Share |
|---|---|---|---|
| 1 | Harness Insure | 12 | 21.8% |
| 2 | NOW Insurance Services | 11 | 20.0% |
| 3 | EverQuote | 5 | 9.1% |
| 4 | DoorDash | 3 | 5.5% |
| 5 | Event Helper | 3 | 5.5% |
| 6 | Gaslamp Insurance Services | 3 | 5.5% |
| 7 | Intuit Quickbooks | 3 | 5.5% |
| 8 | Jotform | 3 | 5.5% |
| 9 | VistaPrint US | 2 | 3.6% |
| 10 | BigTime Software | 1 | 1.8% |
| 11 | Clinton Alford Insurance Agency | 1 | 1.8% |
| 12 | Colonial Surety Company | 1 | 1.8% |
| 13 | floridaregisteredagent.com | 1 | 1.8% |
| 14 | Justworks | 1 | 1.8% |
| 15 | Rocket Lawyer | 1 | 1.8% |
| 16 | SoFi | 1 | 1.8% |
| 17 | The Zebra | 1 | 1.8% |
| 18 | truckinsurancenitic.com | 1 | 1.8% |
| 19 | Waiverforever | 1 | 1.8% |
Ad formats
| Format | Ads shown | Share |
|---|---|---|
| Text ad (advertiser name and headline) | 55 | 100.0% |
| Shopping ad (product name and price) | 0 | 0.0% |
Example ads
12 adsDistinct ads as shown (ignoring capitalization), most frequent first, one per advertiser where possible.
- NOW Insurance ServicesText ad
A Simpler Way to Insure
Shown 11 times
- Harness InsureText ad
Contractor Insurance for Your Business
Shown 8 times
- Event HelperText ad
Single Day Event Insurance
Shown 3 times
- Gaslamp Insurance ServicesText ad
Get General Liability Coverage
Shown 3 times
- EverQuoteText ad
Insurance near you
Shown 3 times
- DoorDashText ad
DoorDash for Merchants
Take food truck orders online
Shown 3 times
- Intuit QuickbooksText ad
Payroll Protection $25K
Shown 2 times
- Clinton Alford Insurance AgencyText ad
Commercial Liability
Shown 1 time
- WaiverforeverText ad
Simplify Waiver Signing
Shown 1 time
- floridaregisteredagent.comText ad
Sunshine Corporate Fillings LLC
Do You Need a Florida Registered Agent?
Shown 1 time
- SoFiText ad
Small Business Loans
Shown 1 time
- truckinsurancenitic.comText ad
National Independent Truckers Insurance Company
Commercial Truck Insurance for Owner-Operators
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 “what business insurance do i need to sign a commercial lease”, after the follow-up message, ChatGPT showed an ad from NOW Insurance Services.
Text ad: “A Simpler Way to Insure”
Fix or choose question · Oct 3, 23:41 ET
In a conversation that began “hiscox small business”, after the follow-up message, ChatGPT showed an ad from Waiverforever.
Text ad: “Simplify Waiver Signing”
Short search question · Oct 4, 05:21 ET
In a conversation that began “Our food truck needs insurance for events and the truck itself, which companies insure food trucks well?”, after the follow-up message, ChatGPT showed an ad from DoorDash.
Text ad: “Take food truck orders online”
Long scenario question · Oct 4, 01:27 ET
In a conversation that began “huckleberry vs pathpoint for small businesses”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Bar Insurance Built for Your Business”
Comparison question · Oct 4, 02:13 ET
In a conversation that began “how do i get insurance for a one day event where the venue requires a certificate”, after the follow-up message, ChatGPT showed an ad from Event Helper.
Text ad: “Single Day Event Insurance”
Fix or choose question · Oct 4, 00:56 ET
In a conversation that began “is a business owners policy worth it for a small retail shop”, after the follow-up message, ChatGPT showed an ad from floridaregisteredagent.com.
Text ad: “Do You Need a Florida Registered Agent?”
Worth it question · Oct 4, 05:03 ET
In a conversation that began “simply business vs coverwallet quotes”, after the follow-up message, ChatGPT showed an ad from EverQuote.
Text ad: “Insurance near you”
Comparison question · Oct 4, 05:45 ET
In a conversation that began “I'm a mobile dog groomer working out of a van, what insurance do I need and which companies cover that?”, after the follow-up message, ChatGPT showed an ad from SoFi.
Text ad: “Small Business Loans”
Long scenario question · Oct 4, 00:42 ET
In a conversation that began “how much does commercial auto insurance cost for one work truck”, after the follow-up message, ChatGPT showed an ad from truckinsurancenitic.com.
Text ad: “Commercial Truck Insurance for Owner-Operators”
Price question · Oct 4, 01:32 ET
In a conversation that began “how much does event liability insurance cost for a vendor at a craft fair”, after the follow-up message, ChatGPT showed an ad from Jotform.
Text ad: “Event Liability Waiver Online Form”
Price question · Oct 4, 04:29 ET
In a conversation that began “how much does product liability insurance cost for a small candle business”, after the follow-up message, ChatGPT showed an ad from VistaPrint US.
Text ad: “Shipped with care”
Price question · Oct 4, 02:09 ET
In a conversation that began “how much does liability insurance cost for a cleaning company with two employees”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Contractor Insurance for Your Business”
Price question · Oct 4, 01:55 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 |
|---|---|---|
| Long scenario | 14 | 25.5% |
| Price | 12 | 21.8% |
| Comparison | 10 | 18.2% |
| Fix or choose | 9 | 16.4% |
| Best for | 8 | 14.5% |
| Short search | 1 | 1.8% |
| Worth it | 1 | 1.8% |
More in Small Business Tools
Other Small Business Tools 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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