From Content to Connection: Rethinking Member Engagement

In this episode of Learning by Association, host Bill Sheehan welcomes Jackson Boyar, CEO and co-founder of RallyBoard, for a wide-ranging conversation on one of the most pressing challenges facing associations today: Meaningful member engagement in an attention economy.

Drawing on his background as the founder of Mentor Collective and his work with associations across industries, Jackson shares why connection is becoming the defining value proposition for associations, particularly for millennials and Gen Z professionals. Together, Bill and Jackson explore how cohort-based programs, peer learning and mentorship can help associations move beyond transactional engagement toward deeper, more authentic member experiences.

The discussion also examines how associations can leverage their unique social capital to differentiate themselves from big tech platforms, create year-round value beyond the annual meeting and rethink engagement, learning and community as strategic drivers of relevance and growth .

Key topics covered in this episode include:

• Why traditional engagement metrics fall short and what real engagement looks like
• The role of cohort-based learning and peer connection in attracting younger members
• How associations can design intentional member experiences that foster trust and loyalty
• The intersection of learning, mentorship and community as a competitive advantage
• Opportunities to scale connection while supporting staff capacity and sustainability

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Chapters

• 0:00 Welcome
• 1:22 Jackson's introduction and founder journey
• 5:59 The membership engagement crisis explained
• 8:35 Helping members find people like them
• 11:57 Turning onboarding and learning into connection moments
• 15:08 Mentorship as a natural outcome of peer groups
• 19:53 What younger professionals really value
• 23:21 Measuring engagement beyond clicks and views
• 26:58 Competing against big tech in the attention economy
• 30:00 Why associations are built for trust and neutrality
• 33:00 Peer learning as a differentiator for the next generation
• 44:07 Peer groups, paid communities and new revenue models
• 54:26 Why connection must come before content

Transcript

Bill Sheehan: 

Welcome to Learning by Association, a podcast brought to you by D2L, where we delve into the ever-evolving world of associations and the challenges they face in navigating the currents of change. I'm Bill Sheehan and I'm thrilled to be your host. Join me and our guests as we explore the role learning plays in driving associations forward and how it can impact every part of your organization, from recruiting to engagement and renewals, to staff development, business strategy, and more. So, let's dive in. 

Hello again, everyone. Bill Sheehan, Global Head of Association Strategy here at D2L, and I'm pretty pumped about this conversation I'm going to have today with Jackson Boyar. He is the CEO and co-founder of RallyBoard. And I ran into, or I was introduced to Jackson at the ASAE event in LA. And we talked about, I think, one of the most important topics right now facing associations is really engagement and bringing in that younger audience to the industry. 

And I think some of the things we're going to talk about today will be very revealing and I think very compelling on how associations really need to adjust. And I think some of the things Jackson's doing with some of his technologies is not only pretty cool, but I think desperately needed within the association space. 

So, without further ado, Jackson, I cannot nearly introduce you as well as you might because you have a pretty cool and impressive background. So, if you could take a few minutes and just introduce yourself and your background and how you got where you are today. 

Jackson Boyar: 

Sure. Well, thank you for having me, Bill. I am a longtime admirer of D2L, coming from the higher ed space now in the association space. So, I'll share a little bit about my story. When I was 24 years old, I made the decision to quit my job and start my first company, which I proceeded to spend 10 years running. That company is called Mentor Collective. It's still operating today and it's the leading mentoring platform for college-aged students entering the workforce. 

So, that was the lens in which I started my career and thinking about learning and professional development. During my time as CEO, we had a wonderful ride, trained over 500,000 mentors, really invested... 

Bill Sheehan: 

Wow. 

Jackson Boyar: 

... deeply in how technology can create deep human connection that sustains and ultimately, helps people prepare for the workforce. But 10 years running a tech company, forced a little bit of burnout onto me. And in my mid-30s, I decided to step back for a year. 

And in reflecting on my first long run professional journey of leadership, the one thing that really did help me deal with burnout and grow more than anything else was being part of a CEO group, which was something that my board afforded me. It was not cheap, but it was transformative to me in my early 30s as a first time CEO. 

I was connected with a number of other education technology founders who had raised a certain amount of capital. We met on a monthly basis and I left that group feeling more connected and supported, but I also wanted to find a similar type of support structure for my team. And at the time, the company was about a hundred employees and I just couldn't find anything cost-effective. I figured our head of HR should have this. The first time on the job customer success manager should have this. 

And as I stepped back from my CEO job to contemplate what my next entrepreneurial journey might look like, I couldn't get that idea out of my head. And I'd spent a lot of time with the higher ed associations at Mentor Collective. We were big sponsors of their work. It was one of the best channels to reach higher education leaders who were buyers of our tool. 

And I started talking to them among others and really stepped into this world of associations about a year and a half ago where I think there are these incredibly rich networks of social capital that if tapped correctly, can provide the type of communal support that I experience as a CEO, but I think is oftentimes out of reach for people that have fewer resources. And so, that was the thrust of the initial mission of RallyBoard. 

Today, we've built a platform that helps associations run cohort-based programs, that notion of your people, your tribe, your group that helps you navigate the workforce, navigate professional loneliness. That's what we're really passionate about supporting. 

And what we've observed in associations is that these programs are often cited as the most transformative membership experiences, and sometimes, they're also embedded into the learning journey within the workforce, but they are incredibly challenging to scale, and that is the niche that RallyBoard occupies today. We want to make it as easy to run a cohort-based peer-to-peer program. And we can go into detail in terms of what that entails, but we want to make that as easy as launching a newsletter, and that's RallyBoard today. 

Bill Sheehan: 

That's a pretty cool... I'm just curious, when you went in and started talking to associations, just for the very first time, how was RallyBoard received? I mean, was there a bit of confusion? What separates this from, let's say, an LMS or a community platform, or was there some of that confusion? 

Jackson Boyar: 

Well, I think my conversation started with the challenges. I didn't want to come in with a bias. I've worked over the years on becoming hopefully a better active listener and not deploying my bias into those conversations. I did have about 70 semiformal interviews with various association leaders before I started down the path of RallyBoard. 

And the themes I heard time and again were challenges engaging younger members of the workforce, Gen Z and millennials, sort of an existential crisis of membership. I've seen stats that it's declined about 20 to 30% over the last two decades within the US at least. And this idea that the association's value proposition is overly tied to the annual meeting. 

In many cases, membership is giving a discount to the annual meeting price tag, but folks are engaging beyond that one-time event. So, the idea of year-round value also kept coming up time and time again. And having spent my first 10 careers as an entrepreneur building online means of folks to engage one-on-one and build relationships without, in that case, the school at the center of the relationship sort of self-organized mentorship. 

I was very interested in ways that members could self-organize and engage within associations. And that's when slowly over time, we started exploring how committees are run today, how special interest groups are run today, how community platforms enable some elements of engagement over time. And the themes we heard were that, yes, there is a digital presence for every association. They can go online, they can take courses, they can post on a community platform in some cases, but there wasn't this depth of authenticity that certainly I experienced in my CEO group that you find in a mentoring relationship. 

It happens at the annual meeting when everybody is there in person and you can have those sort of serendipitous conversations like you and I had, but that's a very rare commodity outside of the in-person experience. And we call it a cohort. Some people call it a mastermind group, a special interest group. 

There are many names for it, but we ultimately started looking at the membership base, maybe there's 5,000, 10,000 members. What percentage of them are getting access to those types of experiences relative to those who want those types of experiences? And I think that's where people started to latch on to what RallyBoard is up to. 

Bill Sheehan: 

Yeah. I think you bring up a good point because associations by their very nature are made up of likeminded individuals and an organization was created or designed to protect, promote, advance that particular industry. And so, everyone initially gets in and say, "Hey, it's pretty cool to be part of this organization because a lot of the same people that are in my discipline or in my career path are members of this association," but it goes deeper than that. 

I mean, when you become a member, it's almost like you don't know what you don't know. What other individuals within this organization are more like me than the rest and then, they form that group. And I think that's difficult to do even at a trade show, but I think in this type of platform that you're creating, they're self-identifying and self-selecting. And I think if they can do it under the auspices of the association's umbrella, now the association not only increases the member engagement, but its relevancy. 

And I think, I'm sure when you were doing your interviewing, you were hearing some of those conversations from association leaders of how do we increase member engagement? How do we increase relevancy and the like? Did you find that to be the case across the verticals? 

Jackson Boyar: 

I don't know if there's research supporting this, but one anecdotal pattern I observed is that the higher specificity of the association's mandate, the greater member engagement they experienced, which I think very much flows into the theory of RallyBoard. If you have an association for Latinos in customer success, as an example, that is an identity-based association, is it a profession-based association? There's a level of lived experience and specificity in that community that is very hard to find out in the general workforce. 

However, if you are a customer success association, if you are a marketing association or a financial analysis association, that's a very broad mandate and inevitably there's going to be a huge diversity of members. And to your point earlier, when somebody joins that association, I think what we know from the research is they're looking for continuing education and they're looking for networking experiences. 

Well, if there's 10,000 members and I am a military veteran, single mother working two jobs, how do I find somebody that represents me? Maybe I can go to the member directory if I have time, which I don't, and hope that the person responds to my email. Maybe I can go post on the general forum, but what we want to offer as an alternative is finding the 5 or 10 people who are most similar to that lived experience within the membership and putting them in a room together, which sounds simple. There's more to it than that, but actually getting that connection to occur is very, very challenging. 

Bill Sheehan: 

So, I want to unpack that just a little bit, because you have touched on, I think, a silver bullet in a way. How do people find each other within that? I mean, for those associations using RallyBoard, how do you educate the industry or the membership that this is available and come in and self-identify, so we can find out and match you or bring you together? 

Because I want to get into mentorship here and I think this is that stepping stone into that and into mentorship because I think that's going to be a critical element. So, how are the associations promoting this, because I think that, to me, is the silver bullet? 

Jackson Boyar: 

Well, there's many ways to promote RallyBoard as there are any sort of member engagement program. I reckon back to our time at Mentor Collective where we found the best marketing channel for a mentorship program was orientation. When you come to campus for the first time and you have that high touchpoint where you're introduced your courses to your cohort, your community. 

I think the same thing holds true in associations. When members first join an association, you have their attention. It might be limited because they're signing up alongside the annual meeting, but that is a moment where you can ask them about their preferences, ask them about who they want to connect with, why they joined the association. 

As another example, maybe you have a high traffic online course that's supported by D2L. And when you take that course, you have the member's attention and you can ask them a couple questions about what they're looking for as they take that course. And if everybody taking that course is asked the same set of questions, you now have the database by which to bring people together on common characteristics. 

So, regardless of the channel of introducing RallyBoard to members, ultimately what we're looking for are member preferences, what they're looking to get out of their member experience. We then use artificial intelligence to analyze that data structured and unstructured and form cohorts on the basis of it. Not just their preferences, but also their scheduling availability. You can't match somebody in Singapore to someone in New York and hope they're going to meet regularly. 

So, there are constraints to work within, but the reality is once you know enough about your members, you can do a lot. The greater the supply of that data, the more specific you can be when matching people together. 

Bill Sheehan: 

Yeah. I think that's a good point. I think you've brought up a good reason why a member or RallyBoard, why a member would want to give you that information. And I think oftentimes, associations are always asking surveying stuff, but it's never clear on why or what they're trying to do with this information. 

And what we've seen at D2L, because we talked to hundreds of associations a week, and what we're seeing, what we're hearing from them is that their members truly want a personalized learning journey. And what I mean by that, it's not just about certification or accreditation, it's just about becoming smarter and day-to-day operations of what I do, and a learning management system can do that pretty well. 

But I think where the engagement is, is you're almost teeing that up to say, it's a stepping stone to other services that the association has to offer with RallyBoard. You're developing this, lack of a better term, a comfort zone where knowledge is exchanged freely and securely, and they feel comfortable in this, and maybe I do want to jump into the LMS, or maybe I do want to jump into the trade show and maybe find revenue to go to that show. 

And so, I'm just curious as when you're seeing this, is that I believe there's a natural component of, I think, of mentorship within RallyBoard. And I think that's so critically important because today's younger generation, as you're probably seeing, they're not quite sure what an association is, why I would join it, what does it do for me? That's expensive. If it's $300 or $200, it's expensive. 

And I really think that mentorship can be that bridge, if you will, between the gaps, because I'm going to date myself here, but when I grew up in associations, we were the original social network. There was no internet. There was no web. We had to go to events, and that was where we exchanged ideas. 

But I think RallyBoard provides maybe a natural opportunity for that mentorship for that older generation to help educate the younger generation on the importance of this association. I mean, and you've probably know mentorship better than anybody, are you starting to see that natural inclination of the mentorship being created by RallyBoard? 

Jackson Boyar: 

Yeah, I think mentoring can happen organically and it can happen in a structured format. So, my first company, Mentor Collective was a very structured approach to mentoring. As you enter a university, as you enter your first employer, we will find somebody within that ecosystem and connect you in a structured mentoring relationship. 

RallyBoard is a space in which unstructured mentoring can occur. So, across our early partners, we have associations running small groups of 5 or 10, and then some, I'd call them medium groups of 20, 30, 40. And in those larger spaces, which the primary engagement is over video chat on Zoom, there's absolutely the opportunity for informal mentoring to occur. 

And in some ways, I would reflect back to the moments in the member journey today where unstructured mentoring can occur, even just putting structured mentoring aside for a moment. It can occur if you meet the right person by chance at the convention at the trade show. But after that, I'm not sure there's so many opportunities. 

You might get a welcoming email, but are you actually getting on the phone with another member? You might get on the phone with staff of the association, but do they have the relevant context professionally to support you in your journey? You might see somebody post something on an online platform that could be relevant to your career, but it's then beholden to you to reach out and understand how to generate that deeper discussion, that deeper connection. 

And if we put the entire burden on the member to find the resources, I think we're doing them a disservice. And much of what RallyBoard preaches, whether you're working with us or any tool, is how can you design the experience proactively so that as part of your onboarding to the association, or at least your first year, you're connected to 5 or 10 professionals who look and feel like you and have similar goals. 

This idea that there is a critical mass of connection within the association that keeps it sticky as a membership, I think is very much true. And I would ask a lot of association leaders to reflect on their first year, how much connection are they intentionally forming for their new members? 

Bill Sheehan: 

Yeah. And it's interesting too, because are you seeing the associations trying to use this mentoring or even RallyBoard, but mentoring more as a strategic member benefit and promoting it as such versus just a program, right? Sometimes they say, "Hey," they'll reach out. "Do you want to be a mentor?" You come into a program. 

To me, that's structured and I think it's not organic and it tends to fall flat, but I think you've touched on it because I think associations, by their very nature, do a lot of things organically, including developing these mentorships. It's natural somebody sees it. Are you working or seeing the associations try to reposition that as a strategic member benefit or advantage of being part of this organization? 

Jackson Boyar: 

Not as much as I would hope, but we're only one year in and we'd hope to spread that gospel, not just my RallyBoard hat, but my relatively young professional hat. I'm in the second half of my 30s, but I think I can speak for the millennial workforce a little bit, and I've reviewed research on Gen Z professional preferences. 

There was a Deloitte study at the beginning of this year that surveyed about 23,000 Gen Z professionals and found connection and learning development to be in one of their top three preferences when choosing an employer. And right next to those, that learning and development driver was also purpose and connection. 

And so, we know that this is why young professionals choose some employers over others. It's probably why they might choose to join a community or an association over not. But I think to your point, they're not fully aware of associations the way prior generations are. And when they run across them, the message, the value proposition doesn't resonate in the way that maybe other paid communities that are not themselves called associations, but function very similarly might resonate. 

And I think it does come down to connection, which is, I think, vastly missing as a support structure in the workforce today. I think associations are perfectly set up to deliver on it, but I think they have to switch their value proposition to speak to the younger members of the workforce. 

Bill Sheehan: 

There's been a bit of a churn in the association space itself amongst staff. And one of the main reasons they're leaving is just, like you said, I'm not being trained. I'm not getting professional development in my own organization, yet we provide it to our members, but I'm not getting it and those type of things. And so, at D2L, we work very closely with them to help them utilize our Brightspace platform in multiple ways to benefit not only the organization, but the membership itself. 

And so, what's happening in the for-profit sector and the corporation sector is also happening in the association. And I think what some associations are not missing, but they got a million things to work on and focus on, but one of those things is their members are expecting that professional development. And professional development, to me, is not just taking tests and getting certified, right? It's other types of things on how to operate. How do I look for a different job? How do I advance my current career? What are those folks that are my age and in a higher position, what separates? How are they different from me? 

And I think they need to have a platform where they can ask these questions openly without being judged or in an environment that they can trust. And I think some of these other technical platforms out there that are competing for the association's members attention and the attention economy, and you touched on this, I think associations are uniquely positioned to rise above the clutter and establish themselves as that single source of truth by providing multiple ways to engage and knowledge exchange. And that's where I think RallyBoard is sitting on a pretty cool area to bring that together. 

Are you seeing, and if you're talking to the associations and looking at some of the analytics, are you seeing a lot of engagement? And what I mean by that is not entering it multiple times over the course of a week, but spending time in there and utilizing it. Are you seeing some of that in the early analytics? 

Jackson Boyar: 

Yeah, I think there's so many dimensions to engagement and somewhat troublingly. I think the industry has gravitated more towards opens and clicks and views, which I would consider to be quite transactional, especially in an industry focused on associating and connecting. 

But what we tend to measure is, do people engage with their cohort in a meeting setting and how long are they spending with one another because that's indicative of the value in those conversations. And we're just about a year in to working with our early partners, but we have cohorts that sometimes meet for two or three hours late into the night because there's sufficient value exchanged in those conversations and people are forming deep connections. 

On average, the meetings will last for about an hour or so. Much of this is up to the association and how they want to structure their cohort-based programming. But I think what it shows is that there's a depth to that connection that you might not see watching an asynchronous video on a website or reviewing a newsletter, you're forming relationships across the association. 

Bill Sheehan: 

Yeah, that's pretty powerful. I mean, that level of engagement is pretty powerful. And I'm wondering too, I think this is a chance what you're creating is really, I think, an opportunity for associations to reposition themselves or rebrand themselves as more in touch and not this whole legacy old association that was founded 110 years ago, but it's actually evolving. 

And I think by your really helping to microdefine in a way, areas of interest within your membership to engage and learn and exceed and advance in your career, I really think that how your position is really offers an opportunity for associations to reposition themselves as being in touch and being part of this movement. Are you starting to see some excitement internally of associations when they're looking at this type of engagement that you're creating? 

Jackson Boyar: 

Absolutely. I think we have to be honest too, that associations have been doing this for many years. In some ways, RallyBoard is not a novel concept. However, one thing I've come to appreciate is how many hats an association leader or team member tends to wear. These are small staffs doing more than the best they can for oftentimes thousands, if not tens of thousands of members. That ratio of association staff to members is astronomical relative to a lot of other corporate American businesses. 

And in that context, I think many of them are running cohort-based programs. There might be the leadership development academy. There might be the volunteer committees, which are themselves a cohort-based program in my mind, but they cap out at 10, 20, 30 cohorts, and it's barely scratching the surface of the scale they could reach. 

And so, we've really tried to embrace what associations are doing already and amplify that work at RallyBoard so that instead of 1% of the membership base getting access, it could be 30, 40, 50% of membership. But I think to your point earlier, as it relates to competitive positioning in the market, we are in an attention economy. And when I think of the messages that would resonate most to my generation and the generation behind me, it is occupying a niche in the attention economy that isn't being fulfilled by big tech. 

I think we have to be honest about how challenging it is for any member-based organization to get the attention of their consumers who are accustomed to going onto TikTok, onto YouTube, onto LinkedIn. YouTube has 30 billion hours of video consumed every month. Reddit has over a billion monthly active users. These are multibillion dollar platforms that are algorithmically teaching us to get addicted to them, and that is very hard to compete against. 

However, these big tech platforms, $300 billion of AI investment into their infrastructure just this year, they're going to invest in the content into capturing our attention. And if an association strategy is, "I'm going to go compete on LinkedIn, on thought leadership by generating blog posts, by running webinars," it's going to be really hard to differentiate against that massive machine of addictive content. Where I think associations can differentiate is the thing that those massive machines have neglected for the last couple decades, which is real genuine connection. 

It is very conveniently also what younger generations are craving. There's an increasing awareness that getting home after work and jumping on TikTok, isn't actually helping me develop professionally. It might be making me feel more lonely. What doesn't make me feel more lonely is connecting with 5 or 10 professionals at other companies in the same role facing the same challenges, which I can do through my association if I was aware of it. 

So, I'm no expert in associations, I'm still ramping up and learning, but when I think about the niche to nail, the message to nail, it's that value proposition because the competition is just going to eat our lunch in the association market. I think associations are about a $30 billion industry a year. Big tech is spending 10 times that number in one year on their AI infrastructure that is going to only get better over time. 

Bill Sheehan: 

That's right. And the fear there too, that's all they do. Those tech companies, they put all of their resources and effort and intellectual capital into that where an association has a myriad of things they have to do. It's the event. It's advocacy. It's government relations. It's education. It's professional development. They have all those things and they're being spread thin. 

And this is where I think that the associations, and I think the Pew Research did a study at the very end of 2024 and into 2025 on what people trust, and they don't trust the media. I mean, it's too one-sided and social media the same way. You're just being influenced by the algorithm and they get addicted quick. But what was rising was nonprofits and associations because of all the information, they gather a lot of information throughout the day and throughout the year and throughout their history and they're sitting on this. 

But the thing I think that separates it is that it's trusted information, it's vetted before it's disseminated, and it's done by subject matter experts within the field. So that information tends to be a little bit more reliable. But what happens is I think what RallyBoard is doing, and even what learning management systems like D2L can do, is you begin to create a sense of loyalty and trust that this information is going to help me, either the dialogue I have or the courses I'm taking are going to help me advance in my career. 

And just like you, D2L spends a lot of time beyond the technology with associations, from instructional design, to surveying to questions, to understanding how each demographic consumes content. And because there's about four to five, depending on what you read, there's about four to five different generations in the workforce right now. 

And each one of them expects something different from the association and it's really hard to deliver them, but I think RallyBoard just leveled that. You can find where you need to be in one fell swoop as opposed to trying to figure out what does Jackson want, what does Bill want, what does David want? 

So, I think what you're bringing to that, the opportunity is to really open up an opportunity for folks to self-select and begin to develop relationships with people of like-minded individuals to pull them away from that social media aspect. It'd be interesting to see, and I don't know if this has been done, are associations starting to see that, because I do believe if they're asking their members, where else do you get your information from, I guarantee you YouTube, TikTok is going to be in there, right? 

Jackson Boyar: 

Yeah. 

Bill Sheehan: 

I don't know if you're seeing any of that. I mean, for them to spend one or two hours within an association platform is awesome. I mean, it's exceptional. 

Jackson Boyar: 

Yeah, I think that would be considered a highly engaged member based on what I've seen. Of course, the converse is the number of hours someone spending on ChatGPT or TikTok or YouTube in a week. I think it's going to be hard to compete those elements of engagement. I think it remains to be seen whether associations can capture the level of attention that big tech can, but I think that that only holds true if associations play the big tech game. 

I wouldn't bet on it in the long term. Some of them will be entrepreneurial and use the tools that big tech are developing to create more engaging member experiences. RallyBoard and other vendors in the space are really trying to lean into leveraging these massive AI investments and making use of them for associations. But I do keep coming back to what an association can provide that nobody else in the economy can. 

If you're an employer, it's very hard to create a group of individuals who are non-biased, who are really committed to your growth as a professional where there is no authority figure in the dynamic because everybody works for that one employer, and forming that cohort is very challenging. It's not going to be a trusted and safe space. 

By contrast, the association in that segment of the economy has folks from every single employer who can speak openly and in a trusting way to one another, and nobody else can do that. Nobody else is aggregating the social networks of all employers, of all members of the workforce in these segments of the economy like the association is. 

And one thing they can do is push out content and try to get everyone's attention. But one thing I think they can lean into successfully is leveraging that network in a way that nobody else can. And whether that's one-to-one mentoring, whether that is running the best annual and regional events on the planet, whether that is creating cohort-based learning programs that are not just asynchronous content, but social learning at the same time, I think those are highly differentiated things. 

I know this because I reviewed as a CEO with a lot of spending authority, I reviewed resources for my team, from HR tech companies, from learning communities, and I could not find something cost-effective, but if I could have gone to the association, every one of my members on my team and for $500,000 given them access to the type of community they so needed outside of my company, it would've been a no-brainer. 

Bill Sheehan: 

Yeah. I think you've touched on something too that is going unfulfilled. And I was giving a presentation about half a year ago to a bunch of association CEOs and the C-suites, and one of the questions they asked me, based upon my experience just being in the industry for 30 years, half of that as an association executive, "What do you think we don't do well?" And I said, "You know what I think it is? You don't promote yourself well. You don't promote yourself as that single source of truth." And I don't think it's on purpose. 

I think associations have... They're built in a bunch of different departments that at times become siloed. I'm not sure what everyone else is doing. We're short-staffed, we're fully burdened. We have a million things we got to do and we really can't stand there and promote and step back and say, "We are that single source of truth." 

Regardless of what you do, be it an HR or you need accounting support, you need government relations support, you need marketing support, we are that organization that does that better than anyone else, and I think you touched on it. Tech companies, at the end of the day, don't really care about that. What they're caring about is, "I want to capture your attention. I want to get you addicted and I want to keep either the engagement so I can sell advertising, get more eyeballs and clicks, or get you to subscribe." 

And I think what associations can do, and I think this is why I was so impressed with what you're doing with RallyBoard is to say, "Hey, we are providing that unmet need for your association at a very," and I don't want to put words in your mouth, but at a very inexpensive way for you to try to compete against that. Are you starting to see that, geez, this is a pretty eye-opening opportunity for us to really establish ourselves as that single source of truth? 

Jackson Boyar: 

Yeah, I don't want to be so bold as to claim we've cracked the code on organizational change in any industry. I will say when I founded Mentor Collective in 2014, many universities were running mentoring programs, but very few at the scale of at least 5 or 10% of the incoming class. 

And with Mentor Collective, every incoming student is able to receive mentorship. And it took us three or five years to really land the message, sort of proliferate the idea that mentoring was core to the undergraduate or graduate student experience. And I think we're up for a similar time horizon with RallyBoard. 

What makes me really excited and bullish about the future is that there are hardly any conversations I have where people aren't nodding their head on the idea that associations have this special asset of a social capital network that can be deployed, and what's exciting too is that many are trying it. 

I speak to association leaders almost every week who are in house running these types of programs for a very small portion of their member base, and the reviews are resounding, but the time constraint in orchestrating is a cause for burnout among association staff. 

And so, as a technologist, that to me is the perfect opportunity to introduce new tools. We know nonprofits don't change overnight. We're happy to be patient. At a minimum, we want to push forward the idea that peer learning is one of the unique tools in the toolkit of an association, as in some ways, they fight for survival. 

One thing we haven't talked about today, but maybe touched on is this idea of the traditional association is very much alive. There is one in almost every field in the economy, but there's also an emergent category of what my generation and younger folks are paying more attention to, it's often a paid community led by a thought leader who maybe has a podcast, has a digital presence. 

I asked the question, what if Ryan Reynolds started an association in marketing? He's a good marketer. He's a great business person and he has tens of millions of people paying attention to what he does. If he overnight said, "Yeah, I'm going to introduce a membership program. We're going to have online courses. We're going to have an annual event. We're going to have a community platform." All of a sudden, the American Marketing Association has very stiff competition. 

And I'm observing that in almost every corner of the economy. Maybe it's not as prevalent as a celebrity starting an association, but I think that's another competitive force out there in the market. And I think what traditional associations have is the legacy and name brand recognition, the authority, the trust that you alluded to. 

But as new members of the workforce enter the economy and are raised on TikTok and watching celebrities and these thought leaders, that will start to erode as well. And so, I'm hopeful that that competitive force is going to drive new innovative adoption, not just RallyBoard, but any number of AI tools that can reach the workforce better. I hope that that will move change a little bit faster. 

Bill Sheehan: 

Yeah. And I think you're starting to see that. I think associations are starting to see that competitive field starting to develop. And again, it's not just organizations, it's really a battle for the attention and the share of the dollar. So, I think an association more than any other type of organization, faces pretty stiff competition, even more so than higher ed institutions, even more so than corporations and private companies. 

They face competition from a variety of different threats, if you will, that they have to deal with on a daily basis. And that's where, I think, Mentor separates itself. The mentorship for those who have been successful in this career, and I think it lends itself to those that are specific, such as doctors and lawyers and accountants and those, they're going to stay in that field most likely for the rest of their career. 

And so, you need those mentors to pull them through. You don't want to be pushed through the industry, you want to be pulled through the industry and ensuing that. And that's why I think what RallyBoard and doing, and to a certain extent, also what D2L does, is it provides a platform for you to really advance your career. And that can be in through networking, through education, through micro-credentialing, through a number of different resources that the association has to offer. 

But what I really think that most of that younger audience is looking for right now, and I mean both from a staff standpoint as well as from a membership standpoint, is that professional development, help me get smarter and advanced. And I think where a lot of that comes from, and we're seeing it on the tech side, is from conversation with other like-minded individuals, and where do they find them, and they're finding them on TikTok. 

I think what you're doing in helping associations is to say, we now have an opportunity and a platform to really level that playing field and increase that engagement where they don't feel that you're always a step away if you're on TikTok or if you're on YouTube, you're always a step away from going completely somewhere else. I can be looking at a video of Ryan Reynolds and the next thing I'm looking at the New York Giants, and I'm God, you've lost me. 

But I think in that environment that you've created, it really is, I think, a safe, secure, developmental type of offering. And I'm wondering, when you go into association to speak with them, what's that tip of the spear, if you will? Who are you going into? Is it the C-suite? Is it the membership person? Is it the learning person? Where do those conversations start? 

Jackson Boyar: 

Yeah. And in our experience so far, it's generally been at the executive level, often a CEO, but there's a scale of an association like our shared partner, PMI, for example. They are a massive global association that we partner with Kelly, their VP of learning. And I think ultimately, it takes a more visionary leader who's either been tasked or wants to reinvent aspects of the association business model. 

I will also say, there are a class of associations I've come into contact with that do make peer connection a core part of their business model. A lot of the associations RallyBoard works with, we are introduced as a member benefit. There's no cost associated when you engage with your peers through a program supported by RallyBoard. 

But I have come across a number of real estate associations, for example, that have paid peer groups embedded into their product offering. And it might be a couple thousands of dollars a year on top of your membership dues to get connected into these highly structured mastermind groups. And this really borrows from nonprofits like YPO or EO, YPO is Young President's Organization, EO, Entrepreneurs Organization. These are both very large nonprofits that are almost entirely funded by mastermind dues. 

So, curating leaders of business into small groups, I think EO's about a $70 million a year nonprofit, YPO is about $200 million a year, almost entirely from the dues of their chapter-based programs where you get matched into a cohort of about 10 other professionals, and that's it. It sounds simple, but people are willing to pay because of the depth of connection that exists in those programs. 

And so, when I'm talking to the CEO or the VP of membership or learning, we're talking about those types of transformations that maybe there's a future where this association is, by an order of magnitude, driving greater member engagement as a benefit of membership, or they're even transforming to the point where their revenue driver is participation in a program like RallyBoard or a mentorship program or a core member benefit that drives something differentiated in the market. 

Bill Sheehan: 

Yeah. And it's interesting, you touched on something that's near and dear to my heart is these organizations that are reliant on dues, which is okay if you can consistently meet those numbers. But one of the other concerns besides engagement and membership satisfaction for associations is non-dues revenue. 

And I think what's happening is the sponsors within the industry, those who are the exhibitors and the ones that provide services to associations, they're getting smarter. And what I mean by that is even like with D2L, we're really looking where we can strategically help an organization advance its cause and by sponsorship and even through administrative support. 

And what I'm seeing, once you create an area that has a lot of engagement and interest, there's going to be a lot of suppliers raising their hands saying, "Can we somehow participate financially in this? " And now, they're coming to you to give you money as opposed to you having to go out and reach them. And I think associations know that it costs a lot of money to run an organization, the platforms and the like. 

And so, they're starting to say, "Hey, how can we help offset some of those costs?" Do you get involved in any of that only because I can see just a natural inclination of non-dues revenue within RallyBoard. There's a natural opportunity there. Are you seeing those offerings? 

Jackson Boyar: 

Well, you put it well when there's a critical mass of engagement and attention, there is an opportunity to drive sponsorships. I know we hate the word monetize, but monetization is what helps an association grow their staff, grow their programming, and create more value in the industry they represent. So, I'm not opposed to that word, but I think it has to be done very thoughtfully. 

And what we're seeing with our early partners is that the engagement occurring in peer groups on RallyBoard is many, many multiples higher than other channels with maybe the exception of the annual meeting. But it's very interesting where a lot of the revenue from an annual meeting comes from. It largely comes from the vendors in the trade show. Those sponsorship dollars pay the bills. 

And so, to the extent RallyBoard and other tools like D2L, can orchestrate that level of engagement in a virtual setting, you've just now introduced another space that sponsors want to engage. And without going into detail, I can say we have several of our early partners already going far down that road. They have major sponsors already within their ecosystem that are recognizing all the people they want to reach are meeting, not once a year at the annual meeting, but weekly or monthly in a shared space on RallyBoard. 

The critical thing that we think about from a product standpoint is how do you do that in a non-transactional way? If I'm a group of CIOs meeting and discussing policy in my world, do I really want the sponsor coming in and engaging with us in a sales call? Absolutely not. So, what are the ways that we can very thoughtfully introduce a sponsor in a non-transactional way, in a value additive way? 

We're pretty excited about some of the experiments we're running, but I'd say it's very much early days for us, and none of this works if engagement doesn't occur. And I'd say 99% of RallyBoard's product attention is on how do we make peer groups, how do we make these virtual spaces of member-to-member connection more vibrant, higher touch, higher depth, more authentic, because that's what we've recognized members crave. And when we do that, many non-dues revenues opportunities will rear their head. 

Bill Sheehan: 

Yeah. I think another thing you're providing to associations too is, we've touched on this throughout our conversation about member engagement. And I think associations historically have had a real tough time really what does engagement mean? Is it, are they opening my newsletter? I send them my magazine, they click that. That's, to me, not engagement. Engagement to me is more of a dialogue versus a monologue. A monologue is opening a newsletter every week or something. 

I think some of the analytics that you might be able to provide or when you're starting to see that within an organization, I think really helps associations not only measure, I think maybe put a parameter around engagement, but also member satisfaction is going to start increasing as well because of this constant dialogue. I mean, do you see some of that too in creating this type of opportunity for members and mentors to engage that satisfaction has got to rise or they wouldn't use it? 

Jackson Boyar: 

Well, I think improving member satisfaction starts with understanding your members. One thing I was a little surprised to find is how many association leaders aren't really, my biased view, fully in touch with their membership. And I can understand if you're a small staff supporting 20, 30,000 members, how hard that can be, especially if you're a global association, but I think there's a real opportunity with technology to be more deeply in touch. 

And one of the additional areas that RallyBoard has built around is not just running peer-to-peer programs, but also learning from your members via peer-to-peer programs. And the power of a cohort is really that it is also in some ways a focus group. Every time members meet and engage, if there are privacy and consent respecting ways to listen in with, even anonymously, without saying who said what in those meetings, but at least getting a sense of what your members are discussing on a monthly or weekly basis, you now have a touchstone to what's happening in the industry. 

And that could inform your strategy, your content development, arc. It can inform all the concurrent sessions at your annual meeting because with a successful RallyBoard implementation, you might have 50 cohorts meeting every single week, and every one of those meetings is an opportunity to learn more about your members if we can solicit the right feedback and package that data the right way. 

Bill Sheehan: 

If you really want to help associations become more efficient, it's instead of trying to figure out what your members want based on surveys that by the time you review them, the marketplace has changed. Why not ... What you're creating is like a focus group in real time consistently. 

And I think the other thing too that you're bringing to bear here is that, and I've been, like I say, my experience in the associations, there always was that 80/20 rule that 80% of your non-dues revenue, for example, was coming from 20% of your suppliers. It's the same way with engagement. It's those rating fans that are coming back and back. And although they're important, the ones you want to worry about is that other 50 or 60% that's not. 

And I think and what they're saying is I don't see a value in participating. And it's not the association's fault, it's just that that particular member doesn't know what the association does. And I think what RallyBoard's bringing to bear is a safe place where knowledge exchange can happen and like-minded individuals can come and speak freely and the association is the beneficiary of this knowledge transfer. I think this is like that next step, if you will, for associations to digitize, for lack of a better word, that feeling they got from the trade show that you had to go to 40 years ago, and I think that's where I think you're uniquely positioned for this too. 

So, I know our time's up. Jackson, this has been one of the fastest hours of the month with you. I can't thank you enough for your time. If there was one thing that you would like to say to associations about the aura that RallyBoard is now producing within that nonprofit space, what do you think that would be? What would be that feeling when associations see RallyBoard as like, "Ah," that aha moment? 

Jackson Boyar: 

Yeah, it might sound trite, but I would say it is a view that associations should reconnect to their namesake associating. I think that's what got us here over a 100 plus years of associating history, and I think that's what's going to get us there in the next 100 years, but we need to come up with more innovative, modern ways of helping folks associate. And I think everyone's figuring this out post-pandemic. 

Everyone's figuring this out in an attention economy where we're in the middle of a loneliness crisis, where we have massive skills gaps developing. And I would posit that connection more so than content is the thing missing, and associations are perfectly positioned to double down in that realm of connection more so than any other organization I've seen on the planet. So, what does that look like? I'm hoping RallyBoard can be a small part of that story, but associations are there for reasons to associate. 

Bill Sheehan: 

Yep. And I think based upon your history, I think you'll be a big part of that movement. So, I wish you and your entire team much success. It was a pleasure meeting you at ASAE, and I can't thank you enough for your time here, and I'm sure we'll stay in touch, but I wish you all the best and appreciate you being on Learning by Association. 

Jackson Boyar: 

Thanks for having me, Bill. 

Bill Sheehan: 

You've been listening to Learning by Association, a podcast where we delve into the ever-evolving world of associations and the challenges they face in navigating the currents of change. 

This episode was produced by D2L, a global learning innovation company, helping organizations reshape the future of education and work. To learn more about our solutions, please visit www.d2l.com, and don't forget to subscribe so you can stay up to date with new episodes. Thanks for joining us, and we'll see you next time.