• Skip to main content
  • Skip to primary sidebar
  • Skip to footer
  • Contact Us

Agency Checklists

Massachusetts Insurance News & Job Opportunities

You are here: Home / Sponsored News / Simply Business Pioneers First-of-its-Kind AI Advisor to Simplify Insurance for Small Business Owners

Simply Business Pioneers First-of-its-Kind AI Advisor to Simplify Insurance for Small Business Owners

October 24, 2025 by AC Editor

AI-powered advisor uses proprietary technology, built on a Retrieval-Augmented Generation (RAG) model

Boston-based Simply Business, LLC, the leading digital marketplace for easily finding, comparing, and buying tailored small business insurance in the U.S., today announced the launch of its first-of-its-kind AI-powered insurance advisor, transforming the insurance buying process for entrepreneurs.

The AI-powered advisor uses proprietary technology, built on a Retrieval-Augmented Generation (RAG) model, to deliver a hyper-personalized, conversational experience that makes the insurance buying process faster, clearer, and more intuitive. The tool assists the small business owner throughout the buying process – answering questions about coverage types, and providing guidance on coverage limits.

The system leverages AI and large language models (LLMs) to intelligently infer user intent and match queries to a robust, human-verified knowledge base ensuring that answers are not only instant but also accurate. The technology features continuous learning capabilities powered by real-time feedback loops, creating a virtuous cycle of self-improvement.

“Our AI-powered insurance advisor is another milestone in our efforts to simplify the insurance buying process for small business owners,” said Dana Edwards, Group CTO at Simply Business. “Importantly, the tool marries advanced technology with the human touch by providing access to our highly skilled agents. We are not just implementing AI; we are pioneering responsible, effective, and scalable solutions that empower entrepreneurs to make confident decisions quickly.”

Since its beta launch, the advisor has led to a 20% higher purchase rate among engaged users. The tool is especially powerful for low-intent visitors. When this group engages with the AI advisor three or more times, the tool acts as an intent multiplier, resulting in a 9% lift in a Request for Quote (RFQ). This demonstrates how it empowers entrepreneurs by cutting through confusion, providing the clarity needed in the insurance buying process.

Simply Business’s dedication to innovation has earned industry recognition, including a Gartner case study spotlighting its insurtech advancements as well as shortlist nominations for ‘AI Implementation of the Year’ from Insurance Insider and for ‘Best Insurtech’ from US FinTech.

About Simply Business

Simply Business is dedicated to making small business insurance simple and accessible. The company’s robust digital marketplace allows small business owners to find and buy the insurance they need online, matching them with coverage from multiple top carriers to offer transparency, choice, and value. Simply Business’s product offering includes general liability, professional liability, business owner’s policy, workers’ compensation, cyber insurance, and more.

An insurtech pioneer, Simply Business has over 20 years of experience supporting the needs of small businesses, with over one million active customers. Founded in the UK in 2005, Simply Business launched its U.S. operations in 2017 and today employs over 1,000 people across offices in London and Northampton in the UK and Boston in the U.S.

Primary Sidebar

MA Division of Insurance Announcements

Free to Listen

Interviews

From Nuptials, Tickets, and Taxes to Trusted Advisor: One Agency’s Unique Path to P&C Success

A Conversation with Evan Silverio, President & CEO of Silverio Insurance Group

Deland, Gibson Celebrates 125 Years: A Conversation with CEO Chip Gibson

The Fourth-Generation Family-Owned Agency is Based in Wellesley

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual | Agency Checklists

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual

Mr. Welch is CEO of Massachusetts-based Hospitality Insurance Group

A Conversation with Daniel C. Bridge – The 2023 Insurance Professional of the Year

Daniel Bridge is Board Chair, President, and CEO of Vermont Mutual Insurance Group

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Our latest Agency Interview is with Nadeen Vella, the founder and owner of a virtual scratch independent agency.

A North Shore Success Story: The $40 Million And Growing Duffy Family of Insurance Agencies

Our latest Agency Interview with Duffy Insurance’s Marc Duffy

More Posts from this Category

InsurOp-Eds

Agency Checklists, MA Insurance News, Mass. Insurance News

A Feast Without the Fiasco: Tips to Help Policyholders Host Safely This Thanksgiving

By AC Editor

Passing of the Torch: Becoming Arbella’s Next CEO

Passing of the Torch: Becoming Arbella’s Next CEO

By Paul Brady

Uninsurable Risk? Maybe Parametric Insurance Is The Answer

By Owen Gallagher

InsurOpEd: Starting A New Chapter in My Life

By Tara Philbin

More InsurOp-Eds

Career News

In Memoriam: Bradford Lowe, 1939-2025

Half a Century of Service Nationwide Honors Six Longtime Employees

SRS Appoints Industry Leader Robert Gagliardi as CEO of SRS Titanium

Strategic Risk Solutions Names Robert Gagliardi CEO of SRS Titanium, Appoints Sandy Bigglestone as Managing Director/CGRCO

Boston Mutual Life Insurance Company Appoints Grant David Ward as New Chief Executive Officer

View More Career News

In Memoriam

In Memoriam: Bradford Lowe, 1939-2025

In Memoriam: Brian Clifford McGrath

In Memoriam: Barbara Comeau, 1948-2025

Company News

PURE Insurance Highlights Teen Driving Risks with New Claims and Parent Insights

Norfolk & Dedham Celebrates 200 Years with Historic Charitable Giving and Community Impact

Norfolk & Dedham Celebrates 200 Years with Historic Charitable Giving and Community Impact

Plymouth Rock Assurance Brings Humor and Humanity to Insurance with New “Keep Calm and Rock On” Brand Campaign 

Arbella Insurance Foundation Celebrates 20th Anniversary by Donating $400,000 to 20 New England Nonprofits

Footer

Agency Checklists

Contact us

We offer a variety of ways to get help promote your company or product.

Announcements
Email Sponsorships
Partnerships
Custom Collaborations

*Affiliate Disclosure

Please note that any of Agency Checklists’ articles might contain one or more affiliate links. This means that any subsequent purchase resulting from these links may result in a commission for us, but at no additional cost to you. For example, as an Amazon Associate, Agency Checklists earns a commission from all qualifying purchases. By working with affiliates we can continue to keep Agency Checklists subscription free. Thank you for your support.

Explore Our Archives

Copyright © 2025 · Agency Checklists · All rights reserved.

 

Loading Comments...