Insurance brokers in Boston that AI assistants recommend

Name: AI assistant recommendations: Insurance brokers in Boston, November 2026
Creator: AIGROW
License: https://creativecommons.org/licenses/by/4.0/

Rogers & Gray Insurance is named most, in 58% of 36 answers.

The ranking

AI Recommendation Rate

1Rogers & Gray Insurance58%
95%: 42 to 73%
ChatGPT
100%
Claude
58%
Gemini
17%
Questions
4 of 4
Avg. position
1.7
Named in answers to
- Who is the best insurance broker in Boston?, from ChatGPT, Claude and Gemini
- I need insurance for my small business in Boston. Which broker would you recommend?, from ChatGPT and Claude
- Which insurance agency in Boston can find me cheaper home and car insurance?, from ChatGPT
- Which independent insurance broker in Boston would you recommend to a family?, from ChatGPT, Claude and Gemini
Also written RogersGray, Rogers & Gray Insurance Agency
Is this your business?
2Eastern Insurance Group56%
95%: 40 to 71%
ChatGPT
67%
Claude
0%
Gemini
100%
Questions
4 of 4
Avg. position
1.5
Named in answers to
- Who is the best insurance broker in Boston?, from ChatGPT and Gemini
- I need insurance for my small business in Boston. Which broker would you recommend?, from ChatGPT and Gemini
- Which insurance agency in Boston can find me cheaper home and car insurance?, from ChatGPT and Gemini
- Which independent insurance broker in Boston would you recommend to a family?, from ChatGPT and Gemini
Is this your business?
3Risk Strategies Company36%
95%: 23 to 52%
ChatGPT
42%
Claude
25%
Gemini
42%
Questions
2 of 4
Avg. position
2.2
Named in answers to
- Who is the best insurance broker in Boston?, from ChatGPT, Claude and Gemini
- I need insurance for my small business in Boston. Which broker would you recommend?, from ChatGPT and Gemini
Also written Risk Strategies
Is this your business?
4Gallagher22%
95%: 12 to 38%
ChatGPT
0%
Claude
67%
Gemini
0%
Questions
4 of 4
Avg. position
2.6
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- I need insurance for my small business in Boston. Which broker would you recommend?, from Claude
- Which insurance agency in Boston can find me cheaper home and car insurance?, from Claude
- Which independent insurance broker in Boston would you recommend to a family?, from Claude
Also written William Gallagher Associates
Is this your business?
5Sullivan Group19%
95%: 10 to 35%
ChatGPT
0%
Claude
0%
Gemini
58%
Questions
3 of 4
Avg. position
2.7
Named in answers to
- Who is the best insurance broker in Boston?, from Gemini
- I need insurance for my small business in Boston. Which broker would you recommend?, from Gemini
- Which independent insurance broker in Boston would you recommend to a family?, from Gemini
Is this your business?
6C&S Insurance14%
95%: 6 to 29%
ChatGPT
42%
Claude
0%
Gemini
0%
Questions
2 of 4
Avg. position
1
Named in answers to
- Which insurance agency in Boston can find me cheaper home and car insurance?, from ChatGPT
- Which independent insurance broker in Boston would you recommend to a family?, from ChatGPT
Is this your business?
7USI Insurance Services14%
95%: 6 to 29%
ChatGPT
0%
Claude
42%
Gemini
0%
Questions
2 of 4
Avg. position
4.6
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- I need insurance for my small business in Boston. Which broker would you recommend?, from Claude
Is this your business?
8Cross Insurance11%
95%: 4 to 25%
ChatGPT
0%
Claude
8%
Gemini
25%
Questions
2 of 4
Avg. position
2
Named in answers to
- I need insurance for my small business in Boston. Which broker would you recommend?, from Claude
- Which insurance agency in Boston can find me cheaper home and car insurance?, from Gemini
Is this your business?
9The Dowd Agencies11%
95%: 4 to 25%
ChatGPT
0%
Claude
33%
Gemini
0%
Questions
2 of 4
Avg. position
2.3
Named in answers to
- Which insurance agency in Boston can find me cheaper home and car insurance?, from Claude
- Which independent insurance broker in Boston would you recommend to a family?, from Claude
Also written Dowd Insurance Agencies
Is this your business?
10Arbella Insurance11%
95%: 4 to 25%
ChatGPT
8%
Claude
0%
Gemini
25%
Questions
2 of 4
Avg. position
2.8
Named in answers to
- Which insurance agency in Boston can find me cheaper home and car insurance?, from ChatGPT and Gemini
- Which independent insurance broker in Boston would you recommend to a family?, from Gemini
Also written Arbella Insurance Group
Is this your business?
11Hub International11%
95%: 4 to 25%
ChatGPT
25%
Claude
8%
Gemini
0%
Questions
2 of 4
Avg. position
3.5
Named in answers to
- Who is the best insurance broker in Boston?, from ChatGPT
- I need insurance for my small business in Boston. Which broker would you recommend?, from ChatGPT and Claude
Also written HUB International
Is this your business?
12Murray Insurance Associates11%
95%: 4 to 25%
ChatGPT
0%
Claude
33%
Gemini
0%
Questions
2 of 4
Avg. position
5.5
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- Which independent insurance broker in Boston would you recommend to a family?, from Claude
Also written Agency Checklists-recommended firms like Murray Insurance Associates
Is this your business?
13Agency Insurance Group8%
95%: 3 to 22%
ChatGPT
0%
Claude
25%
Gemini
0%
Questions
3 of 4
Avg. position
3.7
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- Which insurance agency in Boston can find me cheaper home and car insurance?, from Claude
- Which independent insurance broker in Boston would you recommend to a family?, from Claude
Is this your business?
14Baldwin Insurance Group8%
95%: 3 to 22%
ChatGPT
0%
Claude
25%
Gemini
0%
Questions
2 of 4
Avg. position
4.3
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- I need insurance for my small business in Boston. Which broker would you recommend?, from Claude
Also written Baldwin Risk Partners
Is this your business?
15Rich & Cartmill6%
95%: 2 to 18%
ChatGPT
0%
Claude
17%
Gemini
0%
Questions
2 of 4
Avg. position
1
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- I need insurance for my small business in Boston. Which broker would you recommend?, from Claude
Also written Rich & Cartmill Insurance
Is this your business?
16Gordon Atlantic Insurance6%
95%: 2 to 18%
ChatGPT
0%
Claude
0%
Gemini
17%
Questions
1 of 4
Avg. position
3
Named in answers to
- Which insurance agency in Boston can find me cheaper home and car insurance?, from Gemini
Is this your business?
17Kaplansky Insurance6%
95%: 2 to 18%
ChatGPT
17%
Claude
0%
Gemini
0%
Questions
2 of 4
Avg. position
3.5
Named in answers to
- I need insurance for my small business in Boston. Which broker would you recommend?, from ChatGPT
- Which independent insurance broker in Boston would you recommend to a family?, from ChatGPT
Is this your business?
18Chartwell Insurance Agency6%
95%: 2 to 18%
ChatGPT
0%
Claude
17%
Gemini
0%
Questions
2 of 4
Avg. position
4
Named in answers to
- Which insurance agency in Boston can find me cheaper home and car insurance?, from Claude
- Which independent insurance broker in Boston would you recommend to a family?, from Claude
Is this your business?
19Deland, Gibson Insurance Associates6%
95%: 2 to 18%
ChatGPT
0%
Claude
17%
Gemini
0%
Questions
2 of 4
Avg. position
4.5
Named in answers to
- I need insurance for my small business in Boston. Which broker would you recommend?, from Claude
- Which independent insurance broker in Boston would you recommend to a family?, from Claude
Is this your business?
20The Hilb Group6%
95%: 2 to 18%
ChatGPT
8%
Claude
8%
Gemini
0%
Questions
2 of 4
Avg. position
5.5
Named in answers to
- Who is the best insurance broker in Boston?, from Claude
- I need insurance for my small business in Boston. Which broker would you recommend?, from ChatGPT
Also written The Hilb Group of New England
Is this your business?

Open a row to see each assistant's share of its own answers. Questions counts how many of the four produced the name at least once; position is where it came in the answer's list, 1 being first. 22 more names came up in a single answer and are counted above but not listed.

Insurance brokers in Boston: is this your field?

42different names in 36 answers, 22 of them only once. The assistants change their minds from one answer to the next.

Check whether AI names you

Is this your business?

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AI Visibility Index · November 2026

Asked about insurance brokers in Boston, ChatGPT, Claude and Gemini named Rogers & Gray Insurance most often, in 58% of answers (its AI Recommendation Rate), then Eastern Insurance Group (56%). Across 36 answers they named 42 different businesses, 22 of them only once. Each of four buyer questions was asked three times, in English, in November 2026.

The AI Recommendation Rate is the fraction of the 36 answers that named a business. The range under it is a 95% confidence interval: where two ranges overlap, the gap between those businesses could be chance.

Names are printed as the assistants wrote them. We have not checked that any of them is good, open, or real.

58% of answers named Rogers & Gray Insurance

Answers: 36
Businesses named: 42
Named only once: 22
Named by 2+ assistants: 7 of 20
Named again on a rerun: 52%

Edition November 2026. Download the data

What each assistant said

The same questions, the same number of times, and often different names. Each column is one assistant's top five from the ranking above, with the share of its own answers that named them.

#	ChatGPT	Claude	Gemini
1	Rogers & Gray Insurance100%	Gallagher67%	Eastern Insurance Group100%
2	Eastern Insurance Group67%	Rogers & Gray Insurance58%	Sullivan Group58%
3	Risk Strategies Company42%	USI Insurance Services42%	Risk Strategies Company42%
4	C&S Insurance42%	The Dowd Agencies33%	Cross Insurance25%
5	Hub International25%	Murray Insurance Associates33%	Arbella Insurance25%

Questions about insurance brokers in Boston

How AI assistants recommend insurance brokers

ChatGPT, Claude and Gemini named Rogers & Gray Insurance most often, in 58% of 36 answers, then Eastern Insurance Group (56%) and Risk Strategies Company (36%). The names come from what the assistants answered to four buyer questions in November 2026; we have not checked that any of them is good, open or real.

Not always. ChatGPT named Rogers & Gray Insurance most often (100% of its answers), Claude Gallagher (67%) and Gemini Eastern Insurance Group (100%). 7 of the 20 listed businesses were named by two or more of them.

Each question was asked three times. Of the names an assistant gave for a question, 52% came back in two or more of those runs; the rest came up once. The 95% range beside each rate in the ranking shows how far it could move by chance.

Run the free checker: it asks ChatGPT, Claude, Gemini and Grok two of the Index questions for insurance brokers, with the category and the place already filled in, and shows every answer word for word. About 30 seconds, no sign-up. The page on how AI assistants recommend insurance brokers shows what an owner can work on. Nothing can guarantee that an assistant names you.

Named here? Put it on your site

Every business in the ranking was named in two or more answers. The badge says that and nothing more: no position, because the ranges above do not support one. It links back to this page, so anyone can check.

Correct or remove a listing

<a href="https://aigrow.gg/index/insurance-brokers/boston"><img src="https://aigrow.gg/badges/index/2026-11/insurance-brokers/boston.svg" width="312" height="100" alt="Named by AI assistants: Insurance brokers in Boston, AIGROW AI Visibility Index, November 2026"></a>

The questions

Asked word for word, three times each, to every assistant. The prompt is the one the free scan uses. No web search, no location and no chat history, so every answer starts from the same place.

1Who is the best insurance broker in Boston?
2I need insurance for my small business in Boston. Which broker would you recommend?
3Which insurance agency in Boston can find me cheaper home and car insurance?
4Which independent insurance broker in Boston would you recommend to a family?

How to read this page

The full method

What it measures: Which names these models produce when asked cold, from what they learned in training. It is not a review, a rating or our recommendation, and a business missing here may simply be one the models were never shown.
Why the ranges matter: 36 answers is a sample. Asked again next month, most shares will move by a few points; the ranges say how far they could move by chance alone.
One business, several spellings: Branches, legal suffixes and spellings of one business are merged, and the other spellings are printed under its name. Names that might be two businesses are kept apart.
A name is wrong: If a business here is closed, misnamed or yours and you want it removed, tell us. We correct or remove it when the page is next published.

Where the assistants look

The sites read most often, with web search on, before the assistants answer about this category in the United States. From the AI Source Map: 11 answers.

See every site for this category