Few people understand the importance of trust in the affinity industry better than Dan O'Brien. Having spent his career in the affinity space, he has seen firsthand how trust, innovation, and adaptability have shaped everything from product development to long-term partnerships. Consumers need to trust that their coverage will be there when they need it. Carriers and brokers need to trust that their partners will deliver. For decades, PIMA has built a community where members can rely on one another to navigate an evolving industry, with trust serving as the foundation for every connection.
However, it hasn't always been smooth sailing for carriers throughout the evolution of the affinity insurance market. When Dan stepped into the role of PIMA President in 2014, the affinity market was facing a regulatory crisis. Looking back on that time, Dan recalls the uncertainty in the market: "We were all trying to figure out if we were still going to have an association business. There were question marks as to how long, if we'd even survive."
Now, Dan reflects on the lessons that emerged from this turning point—how to guide an organization through crisis, anticipate industry shifts before they happen, and build the kind of trust that makes long-term success possible. His story proves that success in affinity insurance isn't just about selling products— it's about establishing a foundation people can depend on.
Lesson #1: Embrace Market Disruptions and Turn Challenges into Opportunity
During Dan's PIMA presidency in the mid-2010s, the Affordable Care Act (ACA) forced a massive industry shift. For years, major medical insurance had been a core revenue stream for many PIMA members, but with new regulations in place, that model collapsed.
Carriers were forced to cancel hundreds of millions of dollars in policies. The entire affinity market was left scrambling. "We had to exit," Dan recalls. "We had to terminate hundreds of millions of dollars worth of medical business. But we were all in the same boat—other carriers, TPAs—we were all trying to navigate. Where do we go next?"
For some companies, the ACA meant shutting down major parts of their business. For others, it was an opportunity to evolve. Under Dan's leadership, PIMA launched the Affinity 2020 Taskforce, an initiative aimed at helping members identify new revenue streams, embrace data-driven decision-making, and stay ahead of regulatory shifts. But Dan knew that success in a changing market required more than strategy—it required trust.
"You don't build a reputation on what you're going to do tomorrow," he says. "I had good relationships, New York Life had strong relationships. So, we were able to weather that and then go out and pick up new business to replace the lost business."
Companies that had built trust and credibility over time were able to pivot quickly, replacing lost revenue with supplemental benefits, accident insurance, and other emerging solutions. Those who relied too heavily on the old model struggled to regain their footing.
Dan sees this as a critical lesson for PIMA members today, as every business will face disruption, but those who focus on adaptability and long-term trust will always find new ways to thrive.
Lesson #2: Innovate How You Serve Customers, and You'll Always Stay Ahead
For Dan, the rise of digital technology and the demand for instant, frictionless experiences is the most significant shift he has seen in his career. In the past, insurance applications were filled out by hand, mailed, or faxed, and then sat in a pile waiting for review. Customers scheduled medical exams, submitted lab work, and waited weeks—sometimes months—before receiving an answer. That was the reality of underwriting for decades.
Then, expectations shifted. Technology changed the way people interact with services, and insurance was no exception. Dan saw the shift happening long before the industry fully embraced it. "Everything was paper applications," he says. "And now, obviously, the number of applications we get is minuscule compared to all the stuff that we get digitally."
For some companies, adapting to new technological advancements meant adopting algorithm-driven underwriting, predictive analytics, and digital-first customer journeys. Others refused to change, believing a decades-old process would hold firm. That choice determined which businesses stayed competitive. "It's the old Amazon effect," Dan explains. "Everybody now wants an instant decision… If we take the friction out of it, which we have, now we're able to issue policies up to, in some cases, $1,000,000 without [extensive underwriting procedures]."
Dan believes the most successful companies today don't treat technology as a tool for efficiency alone but as a way to build trust and strengthen customer relationships. "We'd love for when somebody logs on… and all of a sudden, it's like, we know you. We know who you are. What do you want to do? What do you need? That's the end goal for everybody."
For PIMA members today, embracing new technology as both a tool and a seamless way to build trust in a digital world is essential. Customers expect seamless, intuitive experiences. The companies that innovate in how they serve customers—whether through accelerated underwriting, real-time personalization, or frictionless online platforms—will be the ones shaping the future of affinity insurance.
Lesson #3: Master the Retail Mindset to Stay Competitive in an Ever-Changing Affinity Industry
For years, many in the industry have misunderstood what affinity insurance really is. Some see it as a version of group insurance, assuming it operates like employer-based benefits. Others approach it like direct-to-consumer sales, overlooking the unique ways affinity groups interact with their members.
Dan has spent his career working in this space, and he sees it differently. "The affinity business to me has always been this hybrid," he explains. "It's on a group platform, but it's more like retail because we're selling member to member. It's not really this guaranteed issue product. It's not sign up at the office. It's underwritten. So it's almost like individual retail, but it's on a group chassis."
This misunderstanding has led to missteps from companies that tried to "shoehorn" affinity into their traditional business models—a move that often backfires. "You really have to have a commitment to understand the affinity business," Dan says. "Because you have to have group expertise, but you also need a retail mindset."
Often, companies that fail to recognize the retail elements of affinity struggle to meet customer expectations as well. Dan believes the organizations that succeed are the ones that take a direct-to-consumer approach and apply it to the group model rather than trying to do the opposite.
For PIMA members, this distinction is critical. Those who embrace both group dynamics and retail distribution will be the ones who build stronger connections, create sustainable growth, and lead the next evolution of the affinity market.
Carrying the Affinity Market Forward with Strategy and Trust
Looking back on his career, Dan has seen affinity insurance evolve through regulatory shifts, technological advancements, and changing customer expectations. Each challenge reshaped the market, but the companies that stayed ahead were the ones that understood their customers, adapted their distribution models, and embraced innovation.
For PIMA members, those lessons still hold true today. The future will bring new challenges, new customer demands, and new ways of doing business. Dan believes technology will play a defining role in how the industry moves forward. "Expenses keep rising on these programs, and to stay competitive, we have to rein that in. Technology and AI are what I think will make a big difference."
But staying ahead requires more than just keeping up with industry changes. Success comes from learning from those who have navigated disruption before, building lasting connections, and surrounding yourself with the right people. Dan O'Brien's leadership offers a clear takeaway for today's affinity market: companies that anticipate change, invest in the right strategies, and build trust with their customers will be the ones that thrive.
For Dan, PIMA has been an essential part of that process, shaping how he built his career and approached the affinity space. "My first meeting was 30 years ago, and for the past 25 years, I think I've missed only two meetings. I really do believe that if you're going to get into the affinity space, there's no better place to get involved than with PIMA."
Affinity insurance has always been shaped by leaders like Dan, who recognize opportunity in times of change. The next era of the industry will belong to those who commit fully, embrace innovation, and never lose sight of the trust that keeps customers coming back.
Published on March 17, 2025.
PIMA® (Professional Insurance Marketing Association®) is a member-driven trade association focused exclusively on the affinity market.
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