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Massachusetts Insurance News & Job Opportunities

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Latest News

Sign reading 'Vermont Mutual Insurance Group' with an overlaid headline: 'Vermont Mutual To Reorganize As Mutual Holding Company'
Massachusetts low number passenger license plates available through the 2026 RMV lottery

Massachusetts Opens 2026 Low Number License Plate Lottery With 237 Plates Available

July 13, 2026

Massachusetts drivers can apply for the RMV’s 2026 Low Number License Plate Lottery through Aug. 14. The lottery will award 237 coveted passenger plates.

Massachusetts private passenger automobile insurance market share rankings

4th Look 2026: Look 2026: Market Share Report for MA Auto Insurance Marketplace

July 13, 2026

Agency Checklists analyzes April 2026 CAR data, ranking Massachusetts private passenger auto insurers by market share, exposures, and market concentration.

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

4th Look 2026: Market Share Report for MA Commercial Auto Insurers

July 13, 2026

Safety, Commerce and Arbella lead the Massachusetts commercial auto insurance market. See market share rankings, premiums, and carrier concentration.

Insurify announced that its online comparison platform has surpassed 250 million real-time auto insurance quotes for U.S. consumers.

Insurify Surpasses 250 Million Auto Insurance Quotes

July 13, 2026

Cambridge-based Insurify has surpassed 250 million real-time auto insurance quotes, expanding its online comparison platform and consumer insurance data.

Boston ranked last among the nation's 200 largest cities in Allstate's 2026 America's Best Drivers Report, with Worcester and Springfield also ranking near the bottom.

Boston Last For Second Year In Allstate’s Best Driver Report

July 13, 2026

Boston ranked last among the nation’s 200 largest cities in Allstate’s 2026 Best Drivers Report, with Worcester and Springfield also ranking among the bottom five.

Massachusetts prosecutors allege Roof Kings underreported payroll and uninsured subcontractor exposure to avoid workers' compensation insurance premiums.

Grand Jury Indicts In $585K Workers’ Comp Fraud Scheme

July 13, 2026

Roof Kings owner Craig Galligan and his company were indicted on workers’ compensation fraud charges alleging nearly $585,000 in unpaid insurance premiums

Nick Fyntrilakis, President and CEO of the Massachusetts Association of Insurance Agents

Governor Healey Appoints Nick Fyntrilakis to Massachusetts Convention Center Authority Board

July 13, 2026

Governor Healey appointed MAIA President and CEO Nick Fyntrilakis to the Massachusetts Convention Center Authority Board, representing Hampden County.

Sign for Vermont Mutual Insurance Group with logo and brick building in background.

Vermont Mutual To Reorganize As Mutual Holding Company

July 12, 2026

Vermont Mutual is seeking policyholder approval to reorganize into a mutual holding company while preserving mutual ownership and independent agency distribution.

Insurance Coverage Cases

Massachusetts Appeals Court decision expanding third party beneficiary rights under Section 29 payment bond law

Appeals Court Redefines “Contractual Relationship” Under Public Bond Statute

June 15, 2026

Mass. Appeals Court rules third-party beneficiary rights create a “contractual relationship,” avoiding Section 29’s 65-day bond notice requirement.

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.

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Latest Agency Sales

King Risk Partners acquired Perry Insurance Agency of North Andover, Massachusetts, expanding its independent agency footprint in the state.

King Risk Partners Expands Massachusetts Presence with Acquisition of Perry Insurance Agency

July 6, 2026

Sequel Insurance Agencies announced the acquisition of five independent insurance agencies, including Worcester-based Feingold & Feingold Insurance Agency.

SIAA-affiliated Sequel Insurance Agencies Acquires Five Independent Agencies

July 6, 2026

Insurance agency acquisition concept showing partnership and growth between firms

World Welcomes Worcester’s Wolpert Insurance

June 20, 2026

Honor Capital and Ascend are merging to create a unified insurance financial operations platform.

Springfield’s Honor Capital and Ascend Announce Agreement to Merge

June 2, 2026

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DOI News

Massachusetts Auto damage appraiser news

ADALB Moves to Clarify Licensed Appraiser Requirements for Repair Shops

June 20, 2026

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

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CAR News

Massachusetts private passenger automobile insurance market share rankings

4th Look 2026: Look 2026: Market Share Report for MA Auto Insurance Marketplace

July 13, 2026 By AC Editor

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

4th Look 2026: Market Share Report for MA Commercial Auto Insurers

July 13, 2026 By AC Editor

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Insurance Fraud

Massachusetts prosecutors allege Roof Kings underreported payroll and uninsured subcontractor exposure to avoid workers' compensation insurance premiums.

Grand Jury Indicts In $585K Workers’ Comp Fraud Scheme

Roof Kings owner Craig Galligan and his company were indicted on workers’ compensation fraud charges alleging nearly $585,000 in unpaid insurance premiums

Construction site with workers on a roof, a clipboard labeled 'Workers’ Compensation Insurance Fraud' stamped FRAUD, a judge's gavel, and a book of Massachusetts General Laws.

Contractor Indicted For Comp Fraud On Sub Misreps

A Milford contractor was indicted on workers’ comp. insurance fraud charges on allegations that roofing work was misclassified to reduce insurance premiums.

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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

Sign for Vermont Mutual Insurance Group with logo and brick building in background.

Vermont Mutual To Reorganize As Mutual Holding Company

July 12, 2026 By Owen Gallagher

Lemonade has launched its app-based renters insurance platform in Vermont, allowing renters to obtain quotes, purchase policies and file claims digitally

Lemonade Launches Renters Insurance in Vermont With Rates Starting at $5 Per Month

July 7, 2026 By AC Editor

New Hampshire Insurance Department Monitoring NAIC Security Incident

July 6, 2026 By AC Editor

Connecticut recognized as captive insurance domicile of the year highlighting regulatory strength and market growth

Connecticut Named Captive Domicile of the Year at Captive Review Awards USA 2026

June 20, 2026 By Agency Checklists

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Economic & Legislative News in Massachusetts

Massachusetts health care insurance news

Health Insurers Say Drug Costs, Patient Expectations Tightening Cost Bind

June 20, 2026 By State House News Service

Massachusetts insurers propose average 12.9% premium increases for 2027, citing specialty drug costs and rising provider reimbursement rates.

Aviation Insurance Marketplace Massachusetts

Report Flags Insurance Woes for Security, Airport Service Workers

June 20, 2026 By State House News Service

New report finds many union security and airport workers lack affordable health coverage, with high uninsured rates despite employer-sponsored plans.

High school student considering college versus career path decision in classroom setting

Poll: Fewer Parents Expect Their Kids to Pursue Bachelor’s Degree

June 20, 2026 By State House News Service

New polling shows declining interest in four-year degrees among Massachusetts students, with sharp gaps by income, race, and parental education.

Retail shopping scene during Massachusetts sales tax holiday with back to school purchases and checkout activity

Annual Sales Tax Holiday Set for Weekend of Aug. 8-9

June 15, 2026 By State House News Service

Massachusetts will hold its 2026 sales tax holiday Aug. 8–9, suspending the 6.25% tax on most purchases under $2,500.

Boston nightlife scene with restaurants and bars reflecting Massachusetts happy hour and extended last call policy discussion

Healey Throws Support Behind Happy Hour in Pursuit of ‘Vibrancy’

June 15, 2026 By State House News Service

Gov. Healey backs happy hour and extended last call as Massachusetts tests new nightlife policies aimed at boosting business and retaining young residents.

Massachusetts news about the Cannabis Control Commission (CCC)

Court Rejects Bid to Derail Marijuana Ballot Question

June 15, 2026 By State House News Service

Massachusetts SJC rules AG’s summary fair and allows marijuana repeal ballot question to advance toward the November election.

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Company Newswire

The winner of the MAIW/Essex Chapter Scholarship for 2026

The Winners Of The MAIW’s Essex/Middlesex Chapter 2026 Estelle Jeter Scholarship

This is the 88th year of operation for the Massachusetts Association of Insurance Women.

Arbella Insurance Foundation hunger relief campaign supporting food pantries across New England

Arbella Insurance Foundation Raises Over $214,000 for Hunger Relief Programs Across New England

Arbella Insurance Foundation raises $214K for hunger relief, supporting 120 food programs across New England amid rising food insecurity.

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.

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Job Board

Career News

Gavin McPhail, Vice President and Chief Data Officer at Plymouth Rock Assurance.

Plymouth Rock Assurance Strengthens Leadership Team with Three Strategic Appointments 

G. Quinn Landers appointed Senior Vice President and Chief Claims Officer at The Andover Companies

The Andover Companies Appoints G. Quinn Landers Senior Vice President and Chief Claims Officer

Nick Fyntrilakis, President and CEO of the Massachusetts Association of Insurance Agents

Governor Healey Appoints Nick Fyntrilakis to Massachusetts Convention Center Authority Board

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MA Division of Insurance Advertisements

Official Massachusetts Division of Insurance notice from Safeco Insurance of America about an amended Foreign Company License to transact Property & Casualty insurance; dated July 20, 2026.
Official certification: Commonwealth of Massachusetts, Division of Insurance, license amendment for First National Insurance Company of America, 225 Borthwick Ave, Portsmouth, NH, dated July 20, 2026.

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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

Agency Checklists, MA Insurance News, Mass. Insurance News

A Fond Farewell: Frank Mancini Addresses The Big Event Attendees At The Arbella Gourmet Luncheon

By Owen Gallagher

Agency Checklists, MA Insurance News, Mass. Insurance News

InsurOp-Ed – Proposed Uber Bill Keeps Public And TNC Drivers at Risk

By Brian Boucher

Agency Checklists, MA Insurance News, Mass. Insurance News, Micromobility, Bird Scooters, Insurance and scooters

InsurOp-Ed: The Scooter Craze and Insurance

By AC Editor

Agency Checklists, MA Insurance News, Mass. Insurance News, Deland Gibson Insurance, InsurOp-Ed, Talent Shortage in the Insurance Industry

InsurOp-Ed: The Talent Shortage

By Agency Checklists

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In Memoriam

Gordon Elliott Taylor, longtime owner of the Blackmer Insurance Agency in Shelburne, Massachusetts, who served the local insurance community for decades.

In Memoriam: Gordon Elliott Taylor

William R Berkley founder of W R Berkley Corporation and leader in commercial insurance industry

W. R. Berkley Corporation Announces the Passing of Its Founder and Executive Chairman, William R. Berkley

Michael R Quinn longtime leader of Allan M Walker Insurance Agency in Taunton Massachusetts

Taunton Insurance Leader Michael R. Quinn Dies at 70

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