As PIMA approaches its 50th anniversary, we had the opportunity to sit down with former PIMA president Gary Pearl, a key figure in the organization's development and a visionary in the affinity market. From overcoming challenges to redefining standards in technology, Gary's journey offers a unique look at PIMA's evolution throughout the years. His story captures the resilience needed to navigate both challenges and successes, highlighting the vital role of adaptability, innovation, and the power of a united community.
Gary's journey into the affinity insurance industry was rooted in his family's connection to PIMA, where his father had been an original member. However, it was a friend and colleague who encouraged Gary to join a PIMA committee, sparking his own involvement. "I wasn't really giving any thought to it, but [she] actually got me more involved," he recalled. From there, his leadership journey accelerated quickly. Gary was soon on the board, ultimately stepping into the role of president in 2000 during a crucial period of growth and transformation for PIMA.
Reflecting on his time as president, Gary shared pivotal lessons on strengthening organizational continuity within PIMA. He recalled the challenge of a one-year volunteer presidency, explaining, "It was difficult because [PIMA's presidency] is a one-year volunteer position, and you just start to understand the role—and all of a sudden you're done, and the next person is coming in."
Motivated to build lasting stability, Gary championed the professionalization of PIMA's executive leadership roles. This shift, starting with hiring an interim CEO, established a new standard for consistent leadership and set PIMA on a path to long-term impact. Such insights reflect Gary's perspective on PIMA's enduring commitment to professional leadership and a culture of collaboration that continues to thrive today.
Lesson #1: Meet Industry Challenges by Welcoming New Voices
As the affinity insurance market consolidated over the years, independent players like those in PIMA faced mounting pressure to compete with industry giants. For Gary, this shift threatened to erode the close-knit, collaborative environment that defined PIMA's community. "When I was president, there were only a few of us left that stayed independent. Competing with the very large companies was much more difficult when that consolidation happened," he reflected.
To counter these challenges, Gary led initiatives to diversify PIMA's membership, inviting others, such as service providers, to join. Although controversial at the time, these changes expanded PIMA's reach and helped it better support a growing membership base. "We need[ed] to continue to grow. We need[ed] other members…and there just [weren't] enough brokers out there in this specialized niche business," he explained. Gary's efforts helped PIMA stay agile in a shifting market, fostering resilience and inclusivity that have strengthened the organization over the years.
Lesson #2: Don't Underestimate the Power of Collaboration to Drive Collective Success
One of Gary's strongest beliefs is in the power of relationships within PIMA. "Maybe it's because it all started out as these family businesses, but every meeting I go to, there's still long-term relationships," he said. "The relationships are key—being able to pick up the phone and call a friendly competitor and say, 'Hey, how are you overcoming these challenges?' You just don't see [those kinds of relationships] a lot in this industry." This deeply rooted collaborative spirit allows members to grow together and keeps the affinity market dynamic and resilient even in the face of change.
For Gary, this spirit of camaraderie recalls PIMA's earliest days, when founders gathered as both competitors and friends, bound by respect and a shared commitment to the industry. "Even when my dad was involved, they were fierce competitors," he noted, "but they were closer friends and had tremendous respect for each other." Today, this legacy of collaboration continues as Gary's generation passes down the importance of partnership and community to a new wave of industry innovators.
Lesson #3: Shaping Tomorrow Through a Collaborative Spirit and Bold Innovation
Looking ahead, Gary remains optimistic about the future of affinity. Despite a change in traditional types of affinity groups, he sees a promising opportunity for increased relevance and reach. This strength can be largely attributed to PIMA's focus on adapting alongside new technology and its growing community of insurance industry innovators.
His advice to future leaders in the affinity space? Build and sustain strong relationships, especially with others in the industry. "PIMA was great because that's where I learned a lot of things [from] speakers and the content they're bringing into the organization," he said. As the affinity market continues to evolve, Gary believes that collaboration, adaptability, and a commitment to innovation will keep PIMA moving forward—just as they have for the past 50 years.
Gary's work with PIMA highlights the organization's unique culture and adaptability in the face of industry shifts. His legacy of bold decisions and vision has helped shape the affinity market, ensuring PIMA's relevance and strength for the next generation of leaders. For those entering the field, his example makes one thing clear: true leadership means leaving the industry stronger than you found it.
PIMA® (Professional Insurance Marketing Association®) is a member-driven trade association focused exclusively on the affinity market.
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