
Celebrating Independence Was This Year’s Tagline

Massachusetts insurance agents came out in full force this October to celebrate their “independence”. It was an appropriate choice of theme, celebrating both our nation’s 250th anniversary this year as well as the resilience and strength of the Massachusetts independent agency system.
Over four days, the Massachusetts Association of Insurance Agents welcomed over 1,500 agency leaders, along with their team members, producers, carriers, and industry partners from across the Commonwealth to this year’s Big Event at the Sheraton Boston hotel.
The schedule included a wide variety of events, including Continuing Education classes and seminars, the Arbella Gourmet Lunch, the MAIA’s Annual Meeting, networking events, and the Exhibitor trade show, with something for everyone who attended.
Professional development was at the heart of the event, with more than 75 continuing education (CE) credits available across a wide variety of classes. Programming included Accredited Insurance Lines Professional (AILP) Designation and Property & Casualty (P&C) Licensing sessions, leadership opportunities, and insightful discussions on emerging industry trends, including artificial intelligence (AI) and cybersecurity. From earning CE credits and pursuing designations to exploring new ideas and strengthening industry knowledge, Big Event offered something for insurance professionals at every stage of their careers.
“Thank you to everyone who made this year’s Big Event such a memorable celebration,” said Nick Fyntrilakis, President and CEO, MAIA. “From the education sessions and the Trade Show floor to honoring our award recipients and welcoming new board members, this year’s event showed the strength of our independent agency community. We’re already looking forward to seeing everyone again in 2027.”
The MAIA’s Annual Meeting & Investiture of the 2026-2027 MAIA Board of Directors
One of the signature events of the four-day event is the MAIA’s Annual Meeting, which takes place midday Friday before the Arbella Gourmet Lunch. In addition to being a chance to catch up with colleagues and friends, the Annual Meeting is also where the MAIA attends to business and recognizes those members whose leadership and service have helped maintain the strength of the independent agency system.
The Annual Meeting also marked a leadership transition, as Paul Ostrander, CIC, was recognized as MAIA’s incoming Chair, joined by outgoing Chair Richard R. Green, President & CEO Nick Fyntrilakis, and Big “I” Chair Greg Sandrock, CIC, AFIS. The MAIA also welcomed four new members to its Board of Directors: Patrick Powers, LUTCF, CPRIA; Andrew Zawada, CFP, CPA; Ruby Balborda; and Angela Turpin.
In addition, the following awards were given out:
- Henry F. Barry, Jr. Memorial Pacesetter of the Year Award: Charles J. Brophy III
- Board of Directors’ Award: Christopher Cabral, CPCU
- Distinguished Service Awards: Glen Davis, CIC, CRM; Stephen Cohen, CIC, AAI; Christopher Fitts, CIC, CPIA, CPRM; and Shawn McLaughlin
- James O. Herrick Memorial Young Agent of the Year: Evan Dowd
- MAIA’s Chair Award: Richard R. Green, presented by MAIA’s Chair-Elect, Paul Ostrander
The Arbella Gourmet Luncheon
Another fixture on Friday’s schedule is the Gourmet Luncheon hosted by Arbella. Always one of the biggest draws of the four-day event, the luncheon takes place immediately after the Annual Meeting closes. As in past years, the well-attended sit-down luncheon provided an opportunity for old friends and new acquaintances to mingle, as well as to hear from Paul Brady, the president and CEO of Arbella. Joe Torrillo, retired FDNY lieutenant and 9/11 first responder and survivor was the guest speaker at this year’s luncheon.
Selected snaps from the Trade Show
Last, but not least is the Exhibitor’s Trade Show, held on Friday and Saturday of the event. This year’s event drew a full house of companies eager to showcase their products to independent agents. The following is are some photos from the two-day tradeshow

Our Raffle Winner
Finally, Agency Checklists would like to thank everyone who stopped by to say hello at our Booth at the Big Event, and for participating in our raffle.
The winner was Stephanie Boylan from the Morse Insurance Agency. Congratulations!
Finally, a Save the Date: MAIA’s 2027 Big Event will be held September 23–26, 2027, at the Sheraton Boston Hotel, 39 Dalton Street, Boston, MA 02199.
Hope to see you all there.


























