Professional Liability Insurance ads in ChatGPT
Ads shown in ChatGPT conversations about Professional Liability Insurance. We recorded 144 conversations on this topic in logged-out ChatGPT; after the follow-up message, ChatGPT showed 144 ads from 34 advertisers. Most often shown: EverQuote, Jotform and NOW Insurance Services.
Our captureLogged-out ChatGPT, USOct 3–4, 2026
Advertisers shown in Professional Liability Insurance conversations
top 25 of 34Ranked by how many of the conversations on this topic ended with their ad on screen; share of the 144 shown ads.
| # | Advertiser | Ads shown | Share |
|---|---|---|---|
| 1 | EverQuote | 21 | 14.6% |
| 2 | Jotform | 18 | 12.5% |
| 3 | NOW Insurance Services | 15 | 10.4% |
| 4 | Harness Insure | 14 | 9.7% |
| 5 | Ironclad | 14 | 9.7% |
| 6 | Rocket Lawyer | 13 | 9.0% |
| 7 | Gaslamp Insurance Services | 6 | 4.2% |
| 8 | Colonial Surety Company | 5 | 3.5% |
| 9 | foundershield.com | 5 | 3.5% |
| 10 | Event Helper | 3 | 2.1% |
| 11 | Hiscox Insurance Company | 3 | 2.1% |
| 12 | nextinsurance.com | 3 | 2.1% |
| 13 | AGENT CRATE | 2 | 1.4% |
| 14 | GetApp | 2 | 1.4% |
| 15 | Agent Advice | 1 | 0.7% |
| 16 | BBSI | 1 | 0.7% |
| 17 | BigTime Software | 1 | 0.7% |
| 18 | BlackFire Cyber Insurance | 1 | 0.7% |
| 19 | Carta | 1 | 0.7% |
| 20 | Clinton Alford Insurance Agency | 1 | 0.7% |
| 21 | ContractSafe | 1 | 0.7% |
| 22 | Etsy | 1 | 0.7% |
| 23 | Finance Lobby | 1 | 0.7% |
| 24 | Humani HR | 1 | 0.7% |
| 25 | illumend, from myCOI | 1 | 0.7% |
9 more advertisers shared the other 9 shown ads.
Ad formats
| Format | Ads shown | Share |
|---|---|---|
| Text ad (advertiser name and headline) | 143 | 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.
- EverQuoteText ad
Insurance near you
Shown 20 times
- Harness InsureText ad
Contractor Insurance for Your Business
Shown 11 times
- NOW Insurance ServicesText ad
Liability Cover for RNs
Shown 7 times
- Rocket LawyerText ad
Review Contracts Online
Shown 6 times
- JotformText ad
Tax Preparer Agreement Form
Shown 5 times
- Gaslamp Insurance ServicesText ad
General Liability Insurance
Shown 5 times
- IroncladText ad
Contract Review for General Counsel
Shown 4 times
- nextinsurance.comText ad
Fiesta Insurance
Bussines Insurance
Shown 3 times
- foundershield.comText ad
The Baldwin Group Specialty Solutions, LLC
Upgrade basic coverage to match true company scale
Shown 3 times
- Colonial Surety CompanyText ad
Nationwide Surety Bonds
Shown 3 times
- Event HelperText ad
Event Insurance As Low As $67
Shown 2 times
- Clinton Alford Insurance AgencyText ad
Commercial Liability
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 it worth carrying 2 million in e&o instead of 1 million for a growing consulting firm”, after the follow-up message, ChatGPT showed an ad from Rocket Lawyer.
Text ad: “Connect with Attorneys”
Worth it question · Oct 3, 23:04 ET
In a conversation that began “tail coverage cost for e&o”, after the follow-up message, ChatGPT showed an ad from NOW Insurance Services.
Text ad: “A Simpler Way to Insure”
Price question · Oct 3, 23:29 ET
In a conversation that began “average e&o insurance cost for a real estate agent in texas closing 20 deals a year”, after the follow-up message, ChatGPT showed an ad from AGENT CRATE.
Text ad: “New Real Estate Agent? We've Got Your Marketing.”
Price question · Oct 3, 23:21 ET
In a conversation that began “best professional liability for a civil engineer who stamps drawings for small developers”, after the follow-up message, ChatGPT showed an ad from Colonial Surety Company.
Text ad: “Get your contractor bond”
Best for question · Oct 3, 23:14 ET
In a conversation that began “best e&o insurance for a web developer building ecommerce sites for clients”, after the follow-up message, ChatGPT showed an ad from BlackFire Cyber Insurance.
Text ad: “E&O Insurance for Technology Firms”
Best for question · Oct 3, 23:17 ET
In a conversation that began “I'm a structural engineer starting my own firm in Denver, which professional liability insurers handle engineers without crazy premiums?”, after the follow-up message, ChatGPT showed an ad from Harness Insure.
Text ad: “Contractor Insurance for Your Business”
Long scenario question · Oct 4, 04:06 ET
In a conversation that began “I'm a personal trainer who also writes online workout plans in California, do I need professional liability and which insurers cover that?”, after the follow-up message, ChatGPT showed an ad from Insure Fitness Group.
Text ad: “Top Personal Trainer Liability Insurance”
Long scenario question · Oct 3, 23:11 ET
In a conversation that began “alternatives to embroker for startups”, after the follow-up message, ChatGPT showed an ad from Carta.
Text ad: “50K+ Companies Manage Their Equity on Carta”
Comparison question · Oct 3, 23:31 ET
In a conversation that began “cna vs travelers professional liability”, after the follow-up message, ChatGPT showed an ad from Hiscox Insurance Company.
Text ad: “Protect Your Business”
Comparison question · Oct 3, 23:07 ET
In a conversation that began “is e&o insurance worth it”, after the follow-up message, ChatGPT showed an ad from Jotform.
Text ad: “Insurance Certificate Request Form”
Worth it question · Oct 3, 23:17 ET
In a conversation that began “e&o premium went up what now”, after the follow-up message, ChatGPT showed an ad from foundershield.com.
Text ad: “Upgrade basic coverage to match true company scale”
Fix or choose question · Oct 3, 23:16 ET
In a conversation that began “a former client says my advice cost them money and is threatening to sue, what coverage should i have had”, after the follow-up message, ChatGPT showed an ad from Ironclad.
Text ad: “Contract Drafting for General Counsel”
Fix or choose question · Oct 3, 23:09 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 | 19.4% |
| Comparison | 22 | 15.3% |
| Price | 22 | 15.3% |
| Fix or choose | 22 | 15.3% |
| Long scenario | 22 | 15.3% |
| Short search | 14 | 9.7% |
| Worth it | 14 | 9.7% |
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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