Insurance brokers in Boston that AI assistants recommend
We asked ChatGPT and Claude the four questions a buyer asks when looking for insurance brokers in Boston, three times each, in English, and counted who they named. These are the businesses named in two or more of the 24 answers.
Names are printed as the assistants wrote them. We have not checked that any of them is good, open, or real.
- Answers
- 24
- Businesses named
- 33
- Named only once
- 20
- Named by 2+ assistants
- 10 of 13
- Named again on a rerun
- 29%
Edition September 2026. Download the data
Asked for insurance brokers in Boston, ChatGPT and Claude most often named HUB International New England (75% of answers), Kaplansky Insurance (42%) and Risk Strategies (25%). Across 24 answers they named 33 different businesses, 20 of them only once. Each of four buyer questions was asked three times, in English, in September 2026.
The ranking
Share is the fraction of the 24 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.
| # | Business | Share | ChatGPT | Claude | Questions | Avg. position |
|---|---|---|---|---|---|---|
| 1 | HUB International New England | 95%: 55 to 88% | 92% | 58% | 4 of 4 | 1.7 |
| 2 | Kaplansky Insurance | 95%: 25 to 61% | 42% | 42% | 2 of 4 | 1.9 |
| 3 | Risk StrategiesAlso written Risk Strategies Company | 95%: 12 to 45% | 25% | 25% | 2 of 4 | 1.7 |
| 4 | Acrisure New England | 95%: 9 to 41% | 25% | 17% | 2 of 4 | 2.8 |
| 5 | Arbella Insurance | 95%: 7 to 36% | 25% | 8% | 1 of 4 | 2.5 |
| 6 | Cross Insurance | 95%: 7 to 36% | 17% | 17% | 3 of 4 | 2.5 |
| 7 | Eastern Insurance GroupAlso written Eastern Insurance Group LLC | 95%: 4 to 31% | 8% | 17% | 2 of 4 | 3.3 |
| 8 | HUB International Boston | 95%: 2 to 26% | 8% | 8% | 1 of 4 | 1 |
| 9 | HUB International | 95%: 2 to 26% | 0% | 17% | 1 of 4 | 1.5 |
| 10 | Berry Insurance | 95%: 2 to 26% | 8% | 8% | 2 of 4 | 2 |
| 11 | RogersGray Insurance | 95%: 2 to 26% | 0% | 17% | 2 of 4 | 2.5 |
| 12 | Deland, Gibson Insurance Associates | 95%: 2 to 26% | 8% | 8% | 2 of 4 | 3 |
| 13 | H.L. Turner GroupAlso written The H.L. Turner Group | 95%: 2 to 26% | 0% | 17% | 1 of 4 | 3 |
Each assistant column is the share of that assistant's 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. 20 more names came up in a single answer and are counted above but not listed.
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 |
|---|---|---|
| 1 | HUB International New England92% | HUB International New England58% |
| 2 | Kaplansky Insurance42% | Kaplansky Insurance42% |
| 3 | Risk Strategies25% | Risk Strategies25% |
| 4 | Acrisure New England25% | Acrisure New England17% |
| 5 | Arbella Insurance25% | Cross Insurance17% |
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.
<a href="https://aigrow.gg/index/insurance-brokers/boston"><img src="https://aigrow.gg/badges/index/2026-09/insurance-brokers/boston.svg" width="312" height="100" alt="Named by AI assistants: Insurance brokers in Boston, AIGROW AI Visibility Index, September 2026"></a>The questions
Asked word for word, three times each, to every assistant through its API. 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
- 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
- 24 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.
Elsewhere in the Index
Is your business on this list?
The free scan asks the same assistants the questions your customers ask, scores whether they name you, and lists who they name instead.
Edition September 2026 · data under CC BY 4.0