On my flight home from PayrollOrg’s Annual Payroll Congress Convention & Expo (Congress), I was reflecting on the genuine connections the Holmes Corporation team had with PayTrain® customers and PayrollOrg’s staff, members and other vendors attending the conference. It’s such a unique, fun and engaging event that I wish everyone could experience at least once. It made me wonder if I could try to describe PayrollOrg’s secret sauce.
In an era when association conferences compete with virtual conferences, webinars, online learning, and countless other professional development options, PayrollOrg seems to have cracked the code on creating a conference experience that members not only attend but anticipate year after year. Their Congress has achieved something many associations struggle with member loyalty that translates into consistent attendance, enthusiastic participation, and word-of-mouth promotion.
So, what is their secret? They carefully craft an event that addresses the unique needs of their members while creating an experience that feels both professional and personal.
Understanding the Audience
PayrollOrg starts with a deep understanding of their members’ professional experience. Payroll professionals occupy a unique position in the business world—they’re essential to every organization’s operation, but their expertise is often undervalued or misunderstood.
“People outside the area think it’s just pushing a button to generate payroll, but it’s a lot more complicated than that,” explains one Congress attendee. Payroll professionals deal with complex compliance issues, multi-state regulations, tax law changes, and technology integrations that require sophisticated knowledge and careful attention to detail.
More challenging still, payroll departments often exist in organizational limbo. They’re not quite HR, not exactly finance, and their teams are typically small. This isolation can make payroll professionals feel disconnected from their broader organization, creating a need for an external professional community.
PayrollOrg recognizes this reality and positions Congress to fill the need. It’s an annual event where payroll professionals are not just understood but celebrated. Sessions address the sophisticated challenges they face, from navigating regulatory changes to implementing new technologies. More importantly, the entire environment communicates that their expertise matters, and their community understands the key role payroll professionals play in their organizations.
One particularly popular session focused on teaching payroll professionals how to communicate their value to executives through data storytelling. “Payroll professionals tend to be very detailed, and it can be hard to get them to share something in a very high-level way,” notes a Congress attendee. “This kind of coaching on how to talk to executives and use data to get someone to understand our perspective was really valuable.”
PayrollOrg also recognizes payroll professionals through various awards, such as Payroll Man of the Year, Payroll Woman of the Year, Special Recognition, and the Global Vision Award. They have an entire event centered around local chapters and their successes, giving out several awards including Chapter of the Year.
Inclusive Fun for Everyone
PayrollOrg has discovered that loyalty isn’t built through professional content alone—it’s forged through shared experiences that create emotional connections to both the association and fellow members. Their approach to fun is strategic, inclusive, and sophisticated. In fact, fun is one of PayrollOrg’s core values. They believe that fun at work leads to a dynamic company culture, and a dynamic company culture boosts productivity. They work hard but they play hard too!
Congress’ famous costume contest exemplifies this strategy. This year’s Payroll Power Up theme was centered around video games. Our team dressed up as Tetris, taking home 1st prize. Here’s a photo so you understand how all-in we, and other teams, go.
What might seem frivolous in other contexts becomes a powerful community-building tool. With multiple categories and broad participation, the contest creates anticipation, encourages creativity, and provides countless opportunities for interaction and shared laughter.
PayrollOrg extends this inclusive approach to everyone involved in the conference experience. Unlike many events where vendors can feel like outsiders, Congress actively incorporates exhibitors into the fun. “They encourage their vendors to be goofy if they choose and incorporate them in the costume contests, which makes it feel like everyone is included,” observes one attendee.
This inclusion strategy extends to conference staff as well. Leadership, including Executive Director Dan Maddux, actively participate in the social aspects of the conference, making the organization feel accessible and relatable rather than distant and corporate.
The result is an atmosphere where attendees, speakers, vendors, and staff all become part of the same community experience, creating connections that extend beyond this event.
Content That Converts to Action
While the social elements of Congress garner attention, PayrollOrg’s commitment to practical, immediately applicable content is equally important to their loyalty-building strategy. Members return year after year because they consistently leave with knowledge they can implement immediately.
The association stays current with emerging trends affecting their profession. This year’s Congress featured an increased focus on artificial intelligence applications, with real-world examples of how organizations were testing and implementing AI tools in their payroll operations. This wasn’t theoretical discussion—it was practical sharing from peers who had already begun experimenting with new technologies.
PayrollOrg also addresses the communication challenges their members face. Sessions focused on executive communication and data storytelling help payroll professionals articulate their value more effectively within their organizations. This type of professional development addresses a critical need that extends beyond technical payroll knowledge.
The quality and immediacy of the learning content creates a cycle. Members who implement new strategies and see positive results become advocates for both the conference and the association. They return the following year not just as attendees but as success stories, often sharing their experiences in sessions or informal conversations.
The Details That Deliver
PayrollOrg’s loyalty-building strategy succeeds because they understand that the member experience is shaped by countless small details, not just the major program elements. From thoughtfully curated meals to daily photo guides and opportunities for meaningful interaction with staff and leadership, every element is designed with attendee comfort and engagement in mind. These thoughtful touches don’t just enhance the event—they create lasting impact.
Attendees consistently describe the conference as an energizing opportunity for professional growth and networking, leaving them motivated to return to work and share what they’ve learned. By making members feel heard, valued, and connected to a larger professional community, PayrollOrg turns an annual event into a truly memorable experience.
Lessons for Building Your Own Member Loyalty
PayrollOrg’s success offers a guide for associations who want to build deeper member loyalty through their conference experiences:
- Understand your members’ professional reality. What challenges do they face in their workplaces? How does their profession fit (or not fit) within their organizations? Design your conference to address these specific dynamics.
- Create inclusive community experiences. Plan activities that bring all conference participants together, from attendees to vendors to staff. Break down traditional hierarchies through shared experiences.
- Deliver immediately applicable content. Focus on knowledge and skills members can implement right away. Create opportunities for peer-to-peer learning and success story sharing.
- Sweat the small stuff. Pay attention to details that affect members’ comfort and satisfaction. These elements communicate care and professionalism.
PayrollOrg’s Congress succeeds because it serves multiple member needs simultaneously: professional development, community connection, recognition, and fun. By addressing the whole person rather than just the professional role, they’ve created an experience that members actively anticipate and consistently recommend to colleagues.
The result? A conference that builds not just knowledge but genuine loyalty—the kind that transforms members into advocates and ensures long-term association success.
