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Matt Masiello

Matt Masiello

Chief Executive Officer


As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 28 years of experience at SIAA and SAN Group have instilled in him the skills, knowledge, and expertise to lead SIAA and SAN Group (SIAA’s original and largest Master Agency operating across the Northeast). Matt has responsibility for the overall success of both companies, as well as providing strategic vision and leadership for their futures.

SIAA has 48 master agencies covering all 50 states with 13% of all U.S. independent insurance agencies as members, which write over $10 billion in premium, making SIAA the largest national independent insurance agency partnering network.

In his tenure with SIAA and the insurance industry, Matt has:

• Published Insurance Agency 4.0, a book featuring ways independent agents can prepare their agency for the future, develop their digital road map, and increase profit, scalability and time (November 2020).

• Developed SIAA’s internal operations and executed strategic direction.

• Engaged all 48 SIAA Master Agencies in the implementation, operations and growth of their organizations, based on the systems and experience developed in SAN Group; and consulted with Strategic Partner Companies in developing and deepening relationships with SIAA and the Master Agencies across the U.S.

• Contributed to SIAA being ranked number one in Insurance Journal’s Top 20 Agency Partnerships in their 2020 annual Top 100 Report.

• Received the Insurance Business America Hot 100 Award in 2017, which recognizes leaders for shaping the future of the insurance industry. The Hot 100 is a list of the hottest influencers, innovators, and game-changers in America’s insurance industry and is comprised of those who have been nominated by their peers for their influential work in the industry.

• Led SIAA, its member agencies, master agencies and strategic partners in donating over $520,000 combined to Wounded Warriors Project, Dana-Farber Cancer Institute & The Jimmy Fund, as well as Veterans Count, a division of Easter Seals, since 2016.

In the last 28 years, Matt has become a subject-matter expert in the field of insurance and agency development and is a frequent contributor to many industry publications, including Insurance Journal, Property Casualty 360, National Underwriter Magazine, PIA Magazine, Independent Agent, Best’s Review and The Standard. He is a frequent presenter at a variety of insurance conventions, meetings and events.

He has served on regional and national advisory councils for numerous insurance companies and serves on the Board of Trustees of Tilton School.

Matt resides on the seacoast of New Hampshire with his wife and three sons. When not working, you can find him and his family boating, fishing, hiking, traveling, or skiing.