National Association of Insurance and Financial Advisors (NAIFA) President Doug Massey, LUTCF, CLU, ChFC, CRES, FSS, has announced the appointment of Josh O’Gara, CLU, ChFC, CFP, a Partner and Co-Founder at Prism Benefits, PBC, in Woburn, Mass., to serve on the NAIFA Board of Trustees effective immediately.
“Josh O’Gara is a strong addition to NAIFA’s Board of Trustees who brings a wealth of industry experience, a record of leadership success within NAIFA, and a contagious energy,” said NAIFA President Massey. “He is a natural servant-leader who possesses a strong understanding of our association’s membership and advocacy missions. I look forward to working with him for the remainder of this year and in 2026 as the Trustees continue the implementation and execution of the NAIFA 2030 Strategic Plan.”
O’Gara joined NAIFA in 2011 and is a Past President of NAIFA-Massachusetts. Through his NAIFA membership, he developed a passion for political advocacy. He has testified on behalf of NAIFA before the National Conference of Insurance Legislators (NCOIL), officials from the U.S. Department of Labor, and representatives of the U.S. Small Business Administration on the importance of independent contractor status for financial professionals. As NAIFA-Massachusetts President, he led advocacy efforts that resulted in the state adopting the NAIC best interest standard for annuity transactions, encouraged the governor of Massachusetts to veto a bill that would have created a pilot single-payer health coverage program, and helped shape a provision under which the state Department of Insurance offers licensing exams in Spanish. O’Gara serves on NAIFA’s national Grassroots Committee. He regularly attends NAIFA’s Congressional Conference and NAIFA-Massachusetts advocacy events.
“I am honored to join the NAIFA Board of Trustees and look forward to working with President Massey, 2026 NAIFA President Christopher Gandy, and all of my Board colleagues to continue NAIFA’s 135-year record of success,” O’Gara said. “This is an exciting time for our association. We face meaningful challenges but also many more opportunities to grow NAIFA’s membership, maximize our value to members, and bolster our already strong influence as we promote the industry, the community of financial professionals, and the best interests of consumers.”
O’Gara’s appointment fills a vacancy on the board created by the resignation of Trustee John D. Richardson, who has moved on to become the Administrator of Elections for the Nashville, Tenn., area. Richardson’s new career path reflects a passion for politics and service he frequently exhibited as a NAIFA member and leader. O’Gara’s term as Trustee will run through the end of 2026.




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