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Massachusetts Insurance News & Job Opportunities

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Massachusetts Insurance News

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Timely, insightful, and informational news for the Massachusetts insurance industry.

Limited Bus Camera Pilot Found 26,000 Violations

September 29, 2026 by State House News Service

MBTA bus camera enforcement program in Massachusetts

The MBTA says an automated camera enforcement pilot on four buses captured 26,000 bus stop and bus lane violations during a 30-day test as the agency prepares for broader enforcement in 2027.

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

September 28, 2026 by Owen Gallagher

Two businessmen in dark suits pose for a news-style photo; caption reads 'MAPFRE-Safety Merger Creates New Force in Massachusetts P&C Insurance'.

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.

Smaller But Stronger: Insurance Agents in the Age of AI

September 28, 2026 by AC Editor

Independent insurance agency trends and AI adoption in 2026

The estimated number of independent agencies fell to 37,000 in 2026 from 39,000 in 2024, while AI use jumped to 46% and most agencies reported revenue growth.

Big ‘I’ Survey: 87% Say Human Insurance Agent Still Matters

September 22, 2026 by AC Editor

AI in the insurance industry

A new Big “I” survey finds 87% of consumers say having a dedicated insurance agent is important, while 61% are more likely to choose an agent using AI and other modern technology.

Massachusetts Barred His Phony Insurance In 2006. Now Kevin Kolenda Has Pleaded Guilty To Wire Fraud

September 21, 2026 by Owen Gallagher

Kevin Kolenda prize insurance wire fraud case and Massachusetts insurance ban

Nearly 20 years after Massachusetts barred Kevin Kolenda from selling prize insurance without a license, the longtime operator of Hole-in-Won has pleaded guilty to federal wire fraud related to his prize insurance business.

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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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Career News

Chris Taylor, President and CEO of Plymouth Rock’s Independent Agency Group

Plymouth Rock Assurance Corporation names Chris Taylor President and Chief Executive Officer 

Ellen Mann, Vice President of Human Resources at Arbella Insurance Group

Arbella Insurance Group Promotes Ellen Mann to Vice President of Human Resources

After Sixty-Plus Years in “the Best Job in the World”, Warren Buffet Becomes Chairman Emeritus

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In Memoriam

In Memoriam: Stephen Joel Paris, 1938-2026

Jean E. Petersen worked more than 30 years at Kirby Insurance Agency in Whitman, Massachusetts.

In Memoriam: Jean E. Petersen, 1939-2026

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

MA Division of Insurance Announcements

InsurOp-Eds

Agency Checklists, MA Insurance News, Mass. Insurance News

InsurOp-Ed: How to Explain Coinsurance to Clients

By Bill Wilson

Agency Checklists, MA Insurance News, Mass. Insurance News, Scott Collins, Mohawk Insurance, Elevate 2018, Agency Nation's Elevate 2018

MAgent Op-Ed: What A Traditional Brick & Mortar Agent Like Me Learned At Elevate 2018

By AC Editor

Agency Checklists Massachusetts insurance event

InsurOp-Ed: How “Skills-Based Hiring” Could Transform The Insurance Industry

By AC Editor

Passing of the Torch: Becoming Arbella’s Next CEO

Passing of the Torch: Becoming Arbella’s Next CEO

By Paul Brady

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