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Massachusetts Insurance News & Job Opportunities

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massachusetts insurance

InsurOp-Ed: What Big Event 2026 Reminded Me About Our Industry

November 8, 2026 by AC Editor

Heather Kramer shows her patriotic side at the MAIA Big Event 2026

MAIA COO Heather Kramer reflects on this year’s Big Event which united the Massachusetts insurance industry over four days in October 2026.

Executive Director Michael Pezza to Retire from The Insurance Library

November 2, 2026 by Agency Checklists News Desk

The Insurance Library has announced that Executive Director Michael Pezza will retire at the end of December after more than four years leading the 139-year-old Boston institution.

Insurance Rates in 2027: Property Falls as Auto Liability Rises

October 26, 2026 by Owen Gallagher

Willis 2027 insurance forecast showing falling commercial property rates and rising auto liability rates, illustrated by a commercial building and trucks.

Willis’s 2027 insurance market forecast points to continued reductions in commercial property rates while auto liability and excess casualty rates rise. The report also identifies improving high-value homeowners insurance conditions in Massachusetts.

Safety Insurance Shareholders to Vote Nov. 3 on MAPFRE’s $1.54 Billion Acquisition

September 28, 2026 by Owen Gallagher

Safety Insurance Group shareholders will vote Nov. 3 on MAPFRE’s $1.54 billion acquisition. Federal antitrust review has cleared, while Massachusetts Form A approval remains a key regulatory condition to closing.

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The Massachusetts Division of Insurance has withdrawn its long-running enforcement action against former insurance producer John Rapo, ending the case without penalties, findings, or license revocation.

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  • NEW! QUINCY: Legal & Compliance Specialist – Hybrid  (Arbella)
  • NEW! LEOMINSTER: Commercial Lines Account Manager (DeCarolis)
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  • SOUTHBOROUGH: Agency Development Representative (HMIC)
  • YARMOUTH: Employee Benefits Producer – Division Manager (Pioneer Insurance Partners)

Career News

Executive Director Michael Pezza to Retire from The Insurance Library

illustration of AM Best Student Challenge with picture of desk and BU flag in background

Boston University Student Named Finalist in AM Best’s 2027 Student Challenge

Jack Roche, president and CEO of The Hanover Insurance Group, recipient of the 2026 Lifetime Achievement Award

The Griffith Foundation and APCIA Honor John C. Roche with 2026 Lifetime Achievement Award

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MA Division of Insurance Announcements

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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In Memoriam

In Memoriam: James P. Daley, 1959-2026

In Memoriam: Richard Sias, 1946-2026

In Memoriam: Stephen Joel Paris, 1938-2026

InsurOp-Eds

Bindable President Jean Marie Lovett

Bouncing Back: Working to Recover and Rebuild Following COVID-19

By Jean-Marie Lovett

Agency Checklists, MA Insurance News, Mass. Insurance News

InsurOp-Ed: InsurTech Observations – Ten Years Later

By Bill Suneson

Massachusetts Auto damage appraiser news

InsurOp-Ed: My First Auto Claim In 50 Years

By Bill Wilson

Agency Checklists, MA Insurance News, Mass. Insurance News

Mass. Agent Op-Ed: My Volunteer Hurricane Relief Work After Hurricane Harvey

By AC Editor

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