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Massachusetts Insurance News & Job Opportunities

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Latest News

Laptop on a wooden desk showing an auto insurance quotes comparison page with insurer rows and a right-side AI assistant panel.
The Massachusetts Supreme Judicial Court upheld most of the Commissioner's workers' compensation insurance rate decision while remanding two issues for further explanation.

SJC: Commissioner Can Disapprove Comp Rate Filing But Must Explain The 14.6% Rate Cut Order

July 6, 2026

Massachusetts’ highest court upheld most of the Commissioner’s workers’ compensation rate decision while ordering further explanation of two portions of the 2024 ruling.

Cybersecurity concept illustrating the NAIC's report that an Oracle PeopleSoft zero-day vulnerability enabled unauthorized access to portions of its website environment.

NAIC Provides New Details on Cybersecurity Incident, Data Access, and Regulatory Reporting

July 6, 2026

The NAIC said a previously unknown Oracle PeopleSoft vulnerability enabled unauthorized access to portions of its website environment.

The Big I 2026 Market Share Report found independent insurance agencies wrote 62% of U.S. property and casualty insurance in 2025.

Big ‘I’ Report: Independent Agencies Hold 62% of U.S. P&C Market as Industry Results Improve

July 6, 2026

Independent agencies placed 62% of U.S. property and casualty insurance in 2025 as personal lines market share and industry underwriting results improved.

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

King Risk Partners acquired North Andover’s Perry Insurance Agency, continuing its Massachusetts expansion through strategic independent agency acquisitions.

Ryan Towle, President of Davis & Towle Insurance Group, recipient of the Insurance Library's 2026 Insurance Professional of the Year Award.

Ryan Towle To Receive Insurance Library’s 2026 Insurance Professional of the Year Award

July 6, 2026

The Insurance Library named Davis & Towle President Ryan Towle its 2026 Insurance Professional of the Year, recognizing his contributions to the industry.

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

SIAA-affiliated Sequel Insurance Agencies acquired five independent agencies, including Worcester’s Feingold & Feingold.

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

July 4, 2026

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

Insurance agency marketing leads flowing through multiple vendors before telemarketing outreach, illustrating TCPA risks discussed in Ward v. Liberty Mutual.

Ward v. Liberty Mutual: A Lead-Generation Trap for Massachusetts Agencies

June 20, 2026

A federal court’s class certification ruling in Ward v. Liberty Mutual highlights how purchased leads, telemarketing vendors, AI voice tools and TCPA compliance can create major liability for insurance agencies.

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 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

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.

Highway ramp with illuminated wrong way sign and safety technology used to prevent wrong-way driving crashes

Massachusetts Bolstering Efforts to Prevent Wrong-Way Crashes

Massachusetts expands wrong-way driving detection with sensors, signage, and alerts as fatalities rise and safety efforts intensify statewide.

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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

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

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

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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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Career News

Union Mutual Insurance Company President and CEO Lisa Keysar, who announced her retirement effective December 31, 2026.

Union Mutual Celebrates the Career of Lisa Keysar and Announces Next Chapter in Leadership

The winner of the MAIW/Essex Chapter Scholarship for 2026

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

Smiling woman in a dark blazer and blue top, posing for a professional headshot against a neutral gray background.

Sarah Jarvis Joins Vermont Mutual as Vice President and Chief Administrative Officer

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MA Division of Insurance Advertisements

Official notice on Commonwealth of Massachusetts Division of Insurance letterhead dated July 1, 2026, regarding license amendment for OBI America Insurance Company at Plymouth, MN address for Accident and Health insurance in the Commonwealth.
Official notice from the Commonwealth of Massachusetts Division of Insurance about OBI National Insurance Company’s license amendment, dated July 1, 2026, with address block and filing instructions.
Official Massachusetts Division of Insurance notice to General Security National Insurance Company about amending its foreign license to transact property and casualty insurance, dated July 1, 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

Preparing For The Next Pandemic – The Cyber One That Is

By AC Editor

Agency Checklists oped on atten

InsurOp-Ed: Observations And Insights For Insurance Agency Owners About IAOA’s INNOVAT19N

By David Siekman

Agency Checklists, MA Insurance News, Mass. Insurance News, Mass. Insurance Coverage disputes

InsurOp-Ed: 3 Sources of Coverage Gaps That Lead to Claim Disputes

By Bill Wilson

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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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