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Massachusetts Insurance News & Job Opportunities

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Latest News

Three people stand outdoors smiling, with Martha Stewart in the center; banner text reads 'Martha Stewart’s New AI Start-up Homes In On the Home' across the image.
Deland Gibson ranked #13 on Boston Business Journal list of largest Massachusetts insurance brokers

Deland, Gibson Now Largest Independently Owned P&C Agency Headquartered in Massachusetts

May 19, 2026

Deland, Gibson ranks #13 on Boston Business Journal’s list, becoming the largest independent P&C agency headquartered in Massachusetts.

Hint, co-founded by Martha Stewart, plans to combine AI and home expertise to help homeowners proactively manage maintenance, costs, and long-term property value.

Martha Stewart’s New AI Start-up Hint Homes In On the Home

May 19, 2026

Hint, co-founded by Martha Stewart, launches this summer as an AI-powered home management platform that could eventually connect homeowners with maintenance, monitoring, and homeowners’ insurance resources.

Illustration depicting rising cyber insurance claims and ransomware exposure in 2026

Cowbell Report: Cyber Claims Up But Ransom Payments Fall

May 18, 2026

Cowbell’s latest cyber claims report says U.S. cyber insurance losses are rising even as premium volume declines and ransomware tactics evolve.

CopperPoint Insurance Companies and General Indemnity Group logos following acquisition announcement

Boston-based General Indemnity Group to Join CopperPoint in Surety Expansion Deal

May 18, 2026

CopperPoint Insurance will acquire Boston-based General Indemnity Group, adding nationwide commercial and contract surety capabilities to its specialty insurance platform.

TransUnion Q2 2026 report cover with a blue car, city skyline, house model, and charts; headline: Auto Shopping Remains Elevated As Rate Filings Turn Negative.

Auto Insurance Shopping Active As Rate Filings Turn Negative

May 18, 2026

TransUnion says auto insurance shopping remained elevated in early 2026 as rate filings turned negative and competition intensified.

Smiling man in a navy blazer and checkered shirt against a white background (professional portrait).

InsurOp-Ed: The Next Chapter for Independent Insurance Agencies

May 18, 2026

Independent insurance agencies face rising costs and tech demands. Strategic partnerships offer support while preserving independence and client relationships.

BayCoast Insurance recognized as a MAIA Five Star Agency for operational excellence and customer service

BayCoast Insurance Renews Prestigious Five Star Agency Designation

May 13, 2026

BayCoast Insurance renews MAIA Five Star Agency designation, reflecting sustained excellence in operations, customer service, and agency performance.

Insurance Library of Boston Summer Intern Program featuring training, networking, and career development for early-career professionals

Register for the Insurance Library’s 2026 Summer Intern Program!

May 12, 2026

Insurance Library opens registration for its 2026 Summer Intern Program, featuring webinars, in-person events, and 21 hours of training for interns.

Insurance Coverage Cases

Martha’s Vineyard aircraft propeller strike and CGL coverage dispute under Massachusetts law

Court Rules: ‘Regardless of Whether’ In Exclusion Creates Ambiguity

May 4, 2026

A Massachusetts Federal court finds insurer must defend Vineyard hangar operator after $1.45M propeller damage claim.

Massachusetts surplus lines placement and E&O risk documentation

When Limited Market Access Meets Surplus Lines: An E&O Problem

April 27, 2026

Massachusetts producers face E&O risk when surplus lines placements lack documented diligent effort. A breakdown of BR-7, §168, and defensible file practices.

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Latest Agency Sales

Davis & Towle Insurance Group acquisition of Turner Liberty Insurance highlighting independent agency partnership and growth

Davis & Towle Welcomes Turner Liberty Insurance to the Fold

May 18, 2026

Smiling man in a navy blazer and checkered shirt against a white background (professional portrait).

InsurOp-Ed: The Next Chapter for Independent Insurance Agencies

May 18, 2026

Paradiso Insurance Acquired by Trucordia

May 4, 2026

New England insurance agency M&A activity Q1 2026

Insurance Agency Mergers & Acquisitions in Massachusetts | Q1-2026

April 28, 2026

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DOI News

Home Insurance Premiums Rose 12.7% During 2024 says Latest DOI Report

February 2, 2026

DOI Issues Consumer Advisory Regarding Roof-Related Insurance Notices

November 6, 2025

DOI Issues Q&A on Protected Accessory Dwelling Units

October 23, 2025

Insurance Regulators OK Steep Increases, Reject Two as Too Large

July 21, 2025

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CAR News

Massachusetts commercial auto insurance market share and premiums based on CAR data

3rd Look 2026: Market Share Report for MA Commercial Auto Insurers

May 11, 2026 By AC Editor

CAR data shows Massachusetts auto insurance market share trends through Feb. 2026, with top 10 carriers controlling 86.45% of the market.

3rd Look 2026: Market Share Report for MA Auto Insurance Marketplace

May 11, 2026 By AC Editor

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Insurance Fraud

Adroit Health Group Barred in MA — $5M Settlement

Texas Agency Agrees To Pay $5 Million In Restitution and Costs

A Texas-based health agency barred from Massachusetts and will pay $5M over three years for misleading consumers on health insurance coverage .

AI insurance fraud illustration showing manipulated claims and insurer detection challenges

Verisk AI Study Finds Many Would Alter Image For Insurance Claim

A Verisk study finds AI-driven insurance fraud is increasing, with more consumers willing to manipulate claims and insurers struggling to detect altered documents and deepfakes.

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Ratings & Results

AM Best report showing moderation in auto and homeowners insurance rate increases in 2025

Best’s Special Report: Personal Auto and Homeowners Markets’ Stabilization Evident Despite a Decline in Approved Rate Changes

Arrow Mutual Liability Insurance Company rating downgrade illustration showing AM Best downgrade concept

AM Best Downgrades Arrow Mutual Liability Insurance Company Ratings

Liberty Mutual earnings results

Liberty Mutual Posts $2 Billion Quarter as It Shifts from Defense to Growth

Safety Insurance earnings results

$14.3M Q1 Loss For Safety: Back-To-Back Storms’ 1600 Claims Cost $42.7M

Hanover Insurance Q1 2026 results showing improved underwriting, combined ratios, and profitability across P&C segments

Record Q1 Results: The Hanover’s Combined Ratio Improves to 91.7%

Vermont Mutual Insurance Group

Vermont Mutual Annual Meeting Shows Strong Results

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New England Newswire

Davis & Towle Insurance Group acquisition of Turner Liberty Insurance highlighting independent agency partnership and growth

Davis & Towle Welcomes Turner Liberty Insurance to the Fold

May 18, 2026 By AC Editor

Eric Cioppa was Maine's Superintendent of Insurance from 2011 until 2022.

Statement from Commissioner Joan Cohen on Passing of Former Insurance Superintendent Eric Cioppa

May 12, 2026 By AC Editor

Eric Cioppa was Maine's Superintendent of Insurance from 2011 until 2022.

In Memoriam: Eric Cioppa, 1958-2026

May 8, 2026 By AC Editor

Vermont Mutual Insurance Group

Vermont Mutual Annual Meeting Shows Strong Results

May 4, 2026 By AC Editor

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Economic & Legislative News in Massachusetts

Massachusetts debate over rent control ballot measure impacting landlords and tenants

Property Owners Say Costs Outpacing Proposed Rent Caps

May 18, 2026 By State House News Service

Massachusetts rent control debate heats up as Nov. 2026 ballot approaches, with small property owners and housing advocates at odds.

Martha’s Vineyard and Nantucket

Report: Island Real Estate Fees Would Have ‘Minimal’ Impact on Prices

May 18, 2026 By State House News Service

Transfer fee bills remain in committee as lawmakers mull additional responses to affordability crisis

Data center with rows of server racks and blue-lit status LEDs across the cabinets in an expansive room.

Key Senator Says State Lacks Power Capacity for Data Center Expansion

May 12, 2026 By State House News Service

Massachusetts lawmakers debate AI data center growth, citing energy limits, water use, and climate risks as communities push back on development.

Massachusetts guidance on rounding cash transactions as they penny is removed from circulation

As Penny is Phased Out, Retailers Get Rounding Guidance

May 11, 2026 By State House News Service

Massachusetts regulators clarify legal rules for rounding cash transactions as pennies disappear, including sales tax treatment and consumer protections.

Massachusetts officials discuss AI regulation, workforce impact, and government use of ChatGPT technology.

AI Pace Raises Risk, Reward, Regulation Questions

May 8, 2026 By State House News Service

Mass. officials discuss AI regulation, workforce risks, and a “walled-off” enterprise ChatGPT system as lawmakers weigh guardrails and adoption challenges.

Micromobility scooters legislation Massachusetts

Healey Wants Speed Framework to Regulate E-bikes, Scooters

May 4, 2026 By State House News Service

Gov. Healey proposes first-in-the-nation speed-based framework to regulate e-bikes, scooters, and mopeds, enhancing safety and accountability.

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Company Newswire

MassMutual turns 175, Marking Generations of Delivering on its Commitments

MassMutual marks its 175th anniversary, highlighting policyholder focus, $1T in coverage, and a legacy of dividends and community support.

Disney Wild About Safety program relaunch with FM collaboration focused on family safety education and risk awareness

FM and Disney Relaunch ‘Disney Wild About Safety,’ Presented by FM

FM and Disney relaunch the Wild About Safety program, expanding global safety education through updated content and enhanced storytelling.

Patriot Growth Insurance Services new brand identity representing national platform and agency connections

Patriot Growth Insurance Services Refreshes Brand Identity

Patriot Growth Insurance Services debuts a new brand identity, highlighting its national platform, agency connections, and continued expansion.

BayCoast Insurance recognized as a MAIA Five Star Agency for operational excellence and customer service

BayCoast Insurance Renews Prestigious Five Star Agency Designation

BayCoast Insurance renews MAIA Five Star Agency designation, reflecting sustained excellence in operations, customer service, and agency performance.

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Job Board

  • NEW! Commercial Insurance Manager (SalemFive)
  • NEW! FAST Auto Appraiser III (N&D)
  • NEW! REMOTE: Senior Marketing Representative (N&D)
  • BOSTON: Commercial Lines Account Manager (LORE)
  • WOBURN: Sr. Personal Insurance Account Manager (Salem Five)
  • QUINCY: AVP Sales & Marketing (Arbella)
  • YARMOUTH: Commercial Lines Account Manager (Pioneer)
  • SOUTHBOROUGH: President & CEO (Hospitality Insurance Group)
  • SOUTHBOROUGH: Commercial Lines Small Business Account Manager (Fitts)
  • WAKEFIELD: Account Manager – Personal Lines (Hartshorne & Curley)
  • WOBURN: Senior Commercial Lines Account Manager (SalemFive)
  • HOLYOKE: Commercial Lines Account Manager Insurance (Chase Clark Stewart & Fontana Agency)

Career News

Professional headshot of a smiling man in a blue suit against a dark gray background.

Jeffrey C. Johnston Named NAIC Chief Executive Officer 

Patriot Growth Insurance Services appoints Chi Vo as Senior Vice President of Operations to lead agency integration and growth strategy

Chi Vo Joins Patriot Growth Insurance Services as Senior Vice President of Operations

Arbella Insurance leadership transition Bob Bizak retirement Andrew O’Donoghue promotion

Arbella Insurance Group Announces Retirement of Bob Bizak, Executive Vice President of Sales & Marketing 

Risk Strategies founder Michael Christian

King Risk Partners Announces Addition of Michael Christian to Its Board of Directors

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Listen Now

Sponsor

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

Born and Bred in the Bay State: The Special Agent Story

Our Latest Agency Interview is with the Founder & President of Special Agent

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.

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InsurOp-Eds

InSurOp-Ed: One of the Most Often Misinterpreted Liability Exclusions

By Bill Suneson

Agency Checklists, MA Insurance News, Mass. Insurance News

InsurOp-Ed: How to Explain Coinsurance to Clients

By Bill Wilson

Surround Insurance's Kate Terry

Insur OpEd: Four Ways To Improve Your Agency’s Digital Image In No Time At All

By AC Editor

Agency Checklists, MA Insurance News, Mass. Insurance News, Filing An Auto Insurance Claim on my phone, do online auto insurance claims work?

InsurOp-Ed: My First Auto Claim In 50 Years

By Bill Wilson

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In Memoriam

Eric Cioppa was Maine's Superintendent of Insurance from 2011 until 2022.

In Memoriam: Eric Cioppa, 1958-2026

In Memoriam: David H. Knight, 1936-2026

In Memoriam: David H. Knight, 1936-2026

In Memoriam: Saul F. Feingold, 1932-2026

In Memoriam: Saul F. Feingold, 1932-2026

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