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The affinity insurance market has always been about more than just policies—it’s about people. It’s built on trust, relationships, and a shared commitment to serving others. That’s what drew Dave Armstrong to PIMA, and it’s what kept him engaged as he moved from member to board member to PIMA president. 

A 20-year veteran of AIG, Dave spent his career leading in spaces where relationships made all the difference. He joined PIMA’s board in 2014, and by the time he became president in 2019, he had built a deep appreciation for the people who made PIMA what it was. “It’s great to work with talented, fun, successful people, and I think we’ve fortunately had a lot of them.” 

Looking back on his time as president, Dave shares what he’s learned—about resilience, about relationships, and about the future of the affinity market. His story is a testament to the power of steady leadership and a reminder that in times of change, the strongest asset a business can have is the people who stand beside it. 

Lesson #1: The Affinity Market Thrives on Relationships, Not Transactions 

The affinity insurance market has never been just another corner of the industry—it’s built on something deeper. Relationships, trust, and a shared commitment to helping people. That’s what sets it apart. 

Dave saw these traits immediately when he joined PIMA’s board in 2014. The industry was changing fast. “There was a lot of consolidation going on [at] the broker TPAs,” he recalls. “Most of PIMA was originally built on family operations… and as of today, there’s very few left.”  

For many in the industry, such an extensive shift meant watching companies they had spent decades building get absorbed into larger entities. It meant risking losing the personal, relationship-driven way of doing business that had defined affinity for so long. And for those who remained, it meant navigating a landscape where increasing regulations and cybersecurity requirements made it harder than ever to operate independently. 

“Many of the smaller TPAs and brokers just couldn’t afford to keep up with that,” Dave explains. “So what was happening was this consolidation because they had to bring the resources together… not only to build better tools and capabilities for the member experience but also to withstand the onslaught of regulations.”   

Yet even as the market changed, PIMA remained consistent. 

The organization remained a place where competitors weren’t just competitors—they were colleagues, mentors, and, in many cases, friends. Dave remembers seeing this play out time and time again. “The relationships are not just transactional,” he says. “They’re deep, and people do things for each other where they’re not looking to personally profit. It’s more of, ’I’m trying to buy a new technology platform. Can you tell me what you did in your organization?’ Yeah, come on out to my office, and we’ll show you what we did.’ ’And no cost?’ ’Nothing. Just come on out. We’ll show you what we learned.’”  

That kind of support is rare in any industry, but in affinity, it’s the foundation. 

In another example, during the 2008 financial crisis, Dave experienced the power of those relationships firsthand. As CEO of his employer at the time, he was leading an organization that found itself at the epicenter of the meltdown. “I had a front-row seat to the financial meltdown. My company was Ground Zero for it,” he says. “It was a firestorm—media, Congress, everything ... we went through hell.” 

And yet, amidst that chaos, his division didn’t lose a single client. The reason, as Dave explains, is thanks to strong relationships already well-established with members and each other. “Affinity’s all relationships. It really is. You had to have strong relationships to maintain the business during a firestorm.” That’s what makes affinity different, and that’s what makes PIMA different. 

Even today, that culture of trust remains at the heart of the organization. “Most of the people at PIMA are already successful,” Dave says. “They’re there to share knowledge and help versus vying for themselves, which is a very different environment than you get in other places.” That juxtaposition is what makes PIMA unique. It’s a community where the people in the room aren’t just trying to get ahead; they’re trying to help each other succeed. 

Lesson #2: Embrace Innovation Before You Need It and You’ll Never Fall Behind 

One of the defining moments of Dave’s presidency came in the form of PIMA’s response to the COVID-19 pandemic. Though no one could have predicted the crisis, the joint decision to invest in technology and digital tools ahead of time made all the difference. 

“We made a lot of decisions that turned out to be fortuitous,” Dave recalls. At the time, these upgrades didn’t seem urgent—PIMA had always thrived as an in-person organization built on conferences, meetings, and face-to-face networking. But leadership saw the bigger picture. They knew digital connection would play a larger role in the future, even if they couldn’t predict exactly when or how. 

That foresight proved critical, as by the time COVID-19 forced the world into lockdown, neither Dave nor PIMA had to scramble. The organization already had the infrastructure to pivot to virtual engagement, keeping members connected and informed even as the industry faced unprecedented uncertainty. 

Still, the transition wasn’t easy. The low point came in 2021 when PIMA’s New Orleans meeting—typically a hub for in-person networking—was held with more than half of the attendees joining remotely. “It was a ’hold the fort’ mentality,” Dave recalls. “We couldn’t control the pandemic, but we made the investments, and we weathered it. I think the organization came out fabulously as a result of those investments.”  

For Dave, the lesson was clear: if you wait to innovate until you need to, it’s already too late. Because of the groundwork laid before the crisis, PIMA members emerged stronger, more connected, and better prepared for the future. The investments made during Dave’s tenure didn’t just help PIMA get through the pandemic; they set the stage for long-term growth and evolution. 

As the industry continues to change, the lesson remains largely the same. Those who embrace innovation before they need it will always be better prepared for whatever comes next. 

Lesson #3: Look Beyond Traditional Markets and You’ll Find New Opportunities 

One of the biggest misconceptions about the affinity market, according to Dave, is that it’s stagnant. “[People say] there’s no growth in this space. And I think that’s a misconception,” he explains. Rather, one major source of growth opportunity is in adjacent markets. 

For years, affinity was seen as a space dominated by professional associations. But in reality, it sits at the intersection of three key segments: employer-sponsored benefits, direct-to-consumer products, and everything in between. “We’re not just professional associations. We’re affinity groups for sponsored benefits. You have the three segments ... and then we’re in the middle, and our middle’s a pretty big middle.” 

By expanding into adjacent markets, many affinity groups have been able to combat the misconception that there’s no growth. This shift has already begun reshaping the industry at large, but Dave sees an even bigger transformation on the horizon—one driven by advancements in underwriting and digital customer experiences. 

For years, insurance companies have hesitated to fully embrace accelerated underwriting, fearing that they might miscalculate risk. Actuaries justifiably wanted a large sample base before changing tried and true methods. But the demand for faster, more user-friendly experiences has pushed the industry forward. “We’ve been tiptoeing on the accelerated underwriting because the traditional method produced terrific results,” Dave says. “But on the other hand, people expect the Amazon experience, and PIMA carriers are making incredible progress.”  

For PIMA members, it’s important to follow Dave’s example and remember that growth isn’t about waiting for the market to shift—it’s about recognizing where the industry is headed and positioning yourself to lead. 

Strengthening the Future by Learning from the Past 

Dave Armstrong’s leadership at PIMA was shaped by resilience, adaptability, and a deep commitment to relationships. Whether navigating industry consolidation, a global crisis, or the evolution of the affinity market, his approach remained the same—stay ahead of change, invest in the future, and never lose sight of the people you serve. 

Looking back on his time as president, Dave believes these lessons are just as relevant today as they were then. "Do the right thing always. And when you’re faced with an incredible threat, if you’re grounded in ethics and doing the right things with the right people, you can withstand any challenge that you may face."  

For PIMA members, that philosophy is more important than ever. The industry will continue to evolve, consumer expectations will keep rising, and new challenges will emerge. However, as Dave’s journey proves, the organizations that focus on innovation, strategic leadership, and strong relationships will always come out ahead. 

The next chapter of the affinity market is being written now—and the leaders who embrace these lessons will be the ones shaping its future. 

Published on February 21, 2025.