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Massachusetts Insurance News & Job Opportunities

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massachusetts insurance

Update: After Seven Years, the Division of Insurance Dropped Its Case to Revoke John Rapo’s License

June 1, 2026 by Owen Gallagher

The Massachusetts Division of Insurance withdrew its enforcement case against former insurance producer John Rapo.

The Massachusetts Division of Insurance has withdrawn its long-running enforcement action against former insurance producer John Rapo, ending the case without penalties, findings, or license revocation.

Cowbell Report: Cyber Claims Up But Ransom Payments Fall

May 18, 2026 by Owen Gallagher

Illustration depicting rising cyber insurance claims and ransomware exposure in 2026

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

Auto Insurance Shopping Active As Rate Filings Turn Negative

May 18, 2026 by Owen Gallagher

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.

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

Top 10 Inland Marine Insurers | 2022 New England Market Share Reports

August 23, 2022 by AC Editor

A look at the top inland marine insurers in New England.

The Insurance Information Institute & The Institutes To Affiliate

June 30, 2020 by Agency Checklists

The Two Organizations to Unify Their Voices and Modernize Their Capabilities.

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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

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

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

Governor Healey Appoints Nick Fyntrilakis to Massachusetts Convention Center Authority Board

Coverys Elects Insurance Executive Michael L. Boguski to Board of Directors

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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, Lemonade, Lemonade Insurance Policy

InsurOp-Ed: Reverse Engineering – Making Lemons from Lemonade?

By Bill Wilson

InsurOp-Ed: Shrinkflation and Insurance

InsurOp-Ed: Shrinkflation and Insurance

By Bill Wilson

Why Insurance Doesn't Cover the COVID-19 Pandemic

InsurOp-Ed: What Does “Direct Physical Loss Of Or Damage To Property” Mean?

By Bill Wilson

Agency Checklists, MA Insurance News, Mass. Insurance News, Insurance Doorknob Marketing

InsurOp-Ed: Doorknob Marketing

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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