• Skip to main content
  • Skip to secondary menu
  • Skip to primary sidebar
  • Skip to footer
  • Contact Us
  • Post A Job

Agency Checklists

Massachusetts Insurance News & Job Opportunities

  • AC Interviews
  • Agency M&A
  • Career News
  • CAR News
  • DOI News
  • Coverage Cases
  • Innovation
  • InsurOp-Eds
  • AC Podcast
You are here: Home / In Memoriam | Massachusetts / In Memoriam: James Alfred Masiello, 1940-2023

In Memoriam: James Alfred Masiello, 1940-2023

January 9, 2024 by AC Editor

Philanthropist and Public Servant Passes at the age of 83

Jim Masiello passed away December 22, 2023 from a brief illness at the age of 83.

James Alfred Masiello

He established the Masiello Agency in Keene NH in 1965 that became the current Masiello Group which at the time included property and causality insurance, real estate and travel services. The Masiello Agency was the progenerate business entity of many successful companies that are still thriving to this day. Later in his career he started the insurance entities SAN Group in 1983, and then founded Strategic Insurance Agency Alliance (SIAA) in 1995 – reflecting a local, regional, national insurance products delivery system that would lead to unparalleled success in the insurance industry.

He leaves behind a legacy of entrepreneurship and particularly an indelible mark on the insurance industry and the independent insurance agency delivery channel. As the founder of SIAA, the leading national alliance of independent insurance agencies, Jim created a business model that has enhanced the success and bettered the lives of thousands of independent insurance agents and their clients.

Jim was the recipient of numerous recognitions including Person of The Year in Keene, NH in 1982 and the Rough Notes Magazine’s Dr. Henry C. Martin Award of Industry Achievement in 2016 for his commitment to expanding the independent agency system. He also served on a number public and private boards along with insurance company advisory councils.

Jim maintained a lifelong commitment to community involvement and philanthropy mostly centered around improving the community infrastructure of Keene NH his hometown and providing vast educational opportunities for deserving students and their families.

Jim was also a public servant, having served 4 years on the Keene NH planning board and city council along with two terms as the youngest mayor of Keene, NH from 1972 – 1975. As mayor he was instrumental in the development of the cities master plan. He made a bid for the United States Senate in 1978 and served as New Hampshire’s Chairman of the Department of Education. He was an influential figure in the Republican party of New Hampshire as NH Co-Campaign Chair for President Fords election run in 1976 and was proud of his association with President George H. W. Bush leading up to his term as 41st President of the United States.

One of his favorite idioms, “In every challenge lies an opportunity,” served him well throughout his lifetime and is reflected in the successful way he approached all aspects of his life which ultimately lead to a legacy of sustained achievement.

Jim leaves behind his wife Kathy, three children Chris, Lisa and Matt as well as 7 grandchildren and 3 great grandchildren.

Primary Sidebar

Job Board

  • NEW – DEDHAM: Service Operations Representative (N&D)
  • NEW – YARMOUTH: Commercial Lines Account Manager (Pioneer)
  • NEW – SOUTHBOROUGH: Commercial Lines Small Business Account Manager (Fitts)
  • SOUTHBOROUGH: President & CEO (Hospitality Insurance Group)
  • DEDHAM: Service Operations Representative II (N&D)
  • DEDHAM: Senior Actuarial Analyst (N&D)
  • HARRISONBURG, VA: Student Intern – Product Support (N&D)
  • DEDHAM: Senior Service Operations (N&D)
  • DEDHAM: Student Intern – Service Operations (N&D)
  • DEDHAM: Sr. Casualty Claims Adjuster (N&D)
  • WAKEFIELD: Account Manager – Personal Lines (Hartshorne & Curley)
  • WOBURN: Commercial Lines Account Manager (SalemFive)
  • WOBURN: Personal Lines Sales Producer (SalemFive)
  • WOBURN: Commercial Lines Producer (SalemFive)
  • WOBURN: Senior Commercial Lines Account Manager (SalemFive)
  • NORWOOD: Personal Lines Account Manager (SalemFive)
  • HOLYOKE: Commercial Lines Account Manager Insurance (Chase Clark Stewart & Fontana Agency)
  • *URGENT* WOBURN: Private Client Sales Executive (SalemFive)

 

Career News

The Andover Companies Strengthens Executive Team with Senior Leadership Appointments

Liberty Mutual Insurance Appoints Ben Johnson President, Ironshore, Liberty Mutual’s Dedicated US Wholesale Specialty Division

Liberty Mutual Insurance Appoints Ben Johnson President, Ironshore

Openly Announces Independent Board of Directors Appointments

NAAIA Boston Announces 2026 Board of Directors

View All

Listen Now

Sponsor

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.

View All

InsurOp-Eds

RAIS Executive Team On COVID 19 Impact To Massachusetts insurance industry

InsurOp-Ed: COVID19: Forward-looking economic framework for agency planning

By Agency Checklists

InSurOp-Ed: Fried Chicken and Customer Loyalty

By Bill Wilson

Agency Checklists, MA Insurance News, Mass. Insurance News, Insurance Claims, How to make an insurance claim after a natural disaster

InSurOp-Ed: An Agent Call To Action: Underinsurance

By Bill Wilson

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

View All

In Memoriam

In Memoriam: Thomas A. Lawson, 1956-2026

In Memoriam: Thomas A. Lawson, 1956-2026

In Memoriam: Judy Mendolusky, 1943-2026

In Memoriam: Judy Mendolusky, 1943-2026

In Memoriam: J. Joseph Doran, 1930-2026

In Memoriam: J. Joseph Doran, 1930-2026

Footer

Contact us

We offer a variety of ways to get help promote your company or product.

Announcements
Email Sponsorships
Partnerships
Custom Collaborations

*Affiliate Disclosure

Please note that any of Agency Checklists’ articles might contain one or more affiliate links. This means that any subsequent purchase resulting from these links may result in a commission for us, but at no additional cost to you. For example, as an Amazon Associate, Agency Checklists earns a commission from all qualifying purchases. By working with affiliates we can continue to keep Agency Checklists subscription free. Thank you for your support.

Explore Our Archives

Copyright © 2026 · Agency Checklists · All rights reserved.

 

Loading Comments...