This Year’s Groovy Theme Channeled the Sixties
The Massachusetts Association of Insurance Agents celebrated the 60th anniversary of its annual “Big Event” this year. The trade show, which after six decades continues to be one of the largest state associations gathering in the nation, honored the anniversary by debuting a “Groovy” theme for its signature event. The four-day event, held at a new location this year, the Sheraton Boston Hotel, featured a full slate of events from its licensing classes P&C Licensing Classes, to Boston Software’s annual TGIF Friday event, the Arbella Gourmet Luncheon, and the ever-popular trade event.
Another notable change to this year’s event was the date. The convention took place in September from the 26th to the 29th versus previous years when it was held in late October and early November. Next year will continue the new trend with the event scheduled for September 18-21, 2025.
While the rate of consolidation continues in Massachusetts, the Property and Casualty insurance industry continues industry continues to be a dominate force in the Massachusetts economy.
In fact, according to industry market research firm ibisworld, the Property, Casualty, and Direct Insurance industry is the fourth-largest industry per 2024 revenue after Life Insurance & Annuities, Colleges & Universities, and Portfolio Management & Investment Advice. As both part of this ecosystem as well as a leader of small businesses and job creation, the independent agent system in Massachusetts is an integral and vital part of the economy of our Commonwealth.
The MAIA’s Annual Meeting & Investiture of the 2024 MAIA Board of Directors
Fridays are typically the busiest day of the four-day trade event, with the MAIA holding its annual meeting to induct and introduce its Board of Directors for the coming year. Overseen by MAIA President Nick Fyntrialkis and the current MAIA Chairman of the Board, Patrick Dempsey, this year’s meeting also included the presentation of awards to various members of the Association and the swearing in of the MAIA’s Executive Committee Officers and Directors for 2024.
The Arbella Gourmet Luncheon
Another fixture on Friday’s schedule of events is the Gourmet Luncheon hosted by Arbella. Always one of the biggest draws of the four-day event, the luncheon occurs just after the close of the Annual Meeting. As in past years, the well-attended sit-down luncheon offered an opportunity for old friends and new acquaintances to mingle as well as to hear from John Donohue, the president and CEO of Arbella who introduced this year’s guest speaker and newly appointed Big “I” President, Charles Symington.
Benjamin Cavallo, CIC, AAI, CISR Wins the Pacesetter of the Year Award
The Pacesetter of the Year Award is presented annually to a MAIA member agent or local association who, through both their personal and professional life, set an example for their fellow independent agents. The Pacesetter Award is named after former MAIA President and staff member Henry F. Barry, Jr., who both in his personal and professional life “…set an example of hard work, perseverance, compassion, and charity, at a level matched by few in the insurance industry.”
This year’s award was presented to Benjamin Cavallo, CIC, AAI, CISR. Mr. Cavallo is a principal and co-owner of C&S Insurance, headquartered in Mansfield, Massachusetts. Founded in 1959, the agency is currently owned and operated by Mr. Cavallo and his co-principal and owner Keith Signoriello. The two are both the second-generation owners of the agency started together by their respective fathers. It now maintains four locations throughout the state and employs 50+ team members. In addition to running the agency, Mr. Cavallo also has served on the Board of Directors for the Massachusetts Association of Insurance Agents (MAIA) for more than a dozen years and was the Chair of the association in 2022. In 2011, the association named him “Young Agent of the Year,” in recognition of his contributions to the insurance industry.
Recipient Of the James O. Herrick Memorial Young Agent of The Year Award
In 2013, the MAIA renamed the Young Agent of the Year award in honor of former MAIA Board Member, Jim Herrick. A popular and well-regarded member of the Massachusetts insurance industry, Mr. Herrick passed away unexpectedly during the Fall of 2013 at the age of 46.
Mr. Herrick began his insurance career with Toole Insurance in the Berkshires, right out of college. He subsequently moved on to The Hanover Insurance Company where he spent many years before finally joining The Berkshire Insurance Group.
The annual award, presented during the MAIA’s State Annual Meeting, “…seeks to recognize agents who demonstrate leadership in their agency and community and support the mission of the committee by being active participants.”
At this year’s event, the Award was presented to Mamadou Bah of RT Specialty.
Other awards winners during this year’s annual meeting
MAIA’s Chairperson’s Award Recipient, Patrick Dempsey with MAIA’s Chair Elect, Chris Fitts, CIC, CPIA 
Ted Gibson, MLIS is presented with the MAIA Board of Directors’ Award by MAIA Board Chair, Patrick Dempsey 
Distinguished Service Award recipient, Lisa Harbour, CIC, CPCU, with MAIA Board Chair, Patrick Dempsey
The trade show
One of the other major events during the annual MAIA Convention is the trade show, held on the Friday and Saturday days of the event. This year’s event boasted a full house of companies looking to share their products with independent agents. The following are a few of the companies who exhibited this year:
Other candids from this year’s event
As a final wrap-up of this year’s event, the MAIA kindly shared with Agency Checklists all of its photos shown here. The following are some final candid photos from some of the other events during the rest of four-day event.
