When Influencers Disrupt Institutions with Jackson Boyar | [Sidecar Sync Episode 99]

Summary:

Is the future of associations being rewritten by influencers? In this episode, Mallory Mejias is joined by Jackson Boyar, co-founder and CEO of Rallyboard, for a sharp and forward-thinking conversation about how digital creators are reshaping professional learning. They explore the competitive rise of “influencer-led” communities like Josh Bersin Academy, how associations can leverage trust and networks in the AI era, and why curated cohorts could be the key to long-term engagement. If you're an association leader wondering how to remain essential in a rapidly shifting landscape, this one's for you.
Jackson Boyar is the Co-founder and CEO of RallyBoard, a peer learning and engagement platform for associations. He previously served as the Founding CEO of Mentor Collective—higher education’s leading mentorship platform—where he led the company for 10 years and now serves as Chairman of the Board. Under Jackson’s leadership, Mentor Collective partnered with hundreds of universities and employers to support more than 500,000 students, earning a spot on the Inc. 5000 list four years in a row. A 2018 Forbes 30 Under 30 honoree, Jackson is also an active angel investor and advisor to socially minded startups.

https://www.linkedin.com/in/jacksonboyar/
Jackon's LinkedIn Post: https://shorturl.at/5EKqn

Timestamps:

👥Provide comprehensive AI education for your team

https://learn.sidecar.ai/teams

📅 Find out more digitalNow 2025 and register now:

https://digitalnow.sidecar.ai/

🤖 Join the AI Mastermind:

https://sidecar.ai/association-ai-mas...

🔎 Check out Sidecar's AI Learning Hub and get your Association AI Professional (AAiP) certification:

https://learn.sidecar.ai/

📕 Download ‘Ascend 2nd Edition: Unlocking the Power of AI for Associations’ for FREE

https://sidecar.ai/ai

🛠 AI Tools and Resources Mentioned in This Episode:

Galileo Learn ➡ https://getgalileo.ai/learn

Rallyboard ➡ https://www.rallyboard.com

👍 Please Like & Subscribe!

https://www.linkedin.com/company/sidecar-global

https://twitter.com/sidecarglobal

https://www.youtube.com/@SidecarSync

Follow Sidecar on LinkedIn

⚙️ Other Resources from Sidecar: 

• Sidecar Blog
• Sidecar Community
• digitalNow Conference
• Upcoming Webinars and Events
• Association AI Mastermind Group

More about Your Hosts:

Amith Nagarajan is the Chairman of Blue Cypress 🔗 https://BlueCypress.io, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

📣 Follow Amith on LinkedIn:
https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space.

📣 Follow Mallory on Linkedin:
https://linkedin.com/mallorymejias

Read the Transcript

🤖 Please note this transcript was generated using (you guessed it) AI, so please excuse any errors 🤖

[00:00:00] Amith: Welcome to the Sidecar Sync Podcast, your home for all things innovation, artificial intelligence, and associations.

[00:00:14] Mallory: Hello everyone and welcome to today's episode of the Sidecar Sync Podcast. My name is Mallory Mejias, and I'm one of your co-hosts along with Amit Nagar. And on today's episode of the Sidecar Sync Podcast, our guest is Jackson Boyar, an entrepreneur reshaping how associations create connection and value.

[00:00:35] Earlier this year, Jackson wrote a LinkedIn posts that stopped Amme and me in our tracks. In it, he compared the Society for Human Resource Management, also known as with. Members and 75 plus years of history to Thers Academy, a six startup that has already grown. One scale point. Industry [00:01:00] influencers are starting to disrupt legacy associations.

[00:01:03] Jackson knows this space well. He's the co-founder and CEO of rally board a peer learning and engagement platform for associations. Before that, he spent a decade as the founding CEO of Mentor Collective higher education's leading mentorship platform where he supported more than 500,000 students and earned recognition as a Forbes 30 under 30 honoree.

[00:01:26] In this episode, Jackson and I dig into what his post means for you, what it means for associations. We talk about why infrastructure versus influence is one of the biggest challenges. Leaders need to understand how bundling versus unbundling strategies change the way members experience value, and why Jackson believes the future of professional learning won't be owned.

[00:01:50] No, it'll be earned. If you're curious about how associations can stay relevant in the age of influencers, startups, and ai, you don't [00:02:00] wanna miss this conversation. Everybody. Please enjoy this conversation with Jackson Boyar

Jackson. Welcome to the Sidecar Sync Podcast. We're so happy to have you on, first and foremost, like we do in all of our interviews.

[00:02:13] I want you to share a little bit about your background and what kind of has brought you to this moment on the Side Cursing Podcast, this moment in your life.

[00:02:22] Jackson: Thanks, Mallory. Happy to be here. So you can think of me as a serial social entrepreneur, much like Amis. Uh, I started my entrepreneurial career about 11 or 12 years ago as the founding CEO of a company called Mentor Collective, which today is higher education's leading mentoring platform.

[00:02:44] And, uh, like many founders, I didn't wake up in the morning expecting to start a business. I stumbled into it. In this case through a pro bono side project where, uh, my co-founder and I started helping colleges support the [00:03:00] onboarding and success of students entering their institutions and over time found that we could make a living doing that work.

[00:03:07] And over a 10 year journey, uh, built mentor collective into what it is today, uh, at. At one point in that journey, I decided I wanted to go back to the early stages of entrepreneurship. So I took some time off, did a lot of, uh, life admin work, got engaged, uh, and started exploring the world of associations.

[00:03:29] Um, I've always been deeply passionate about social mobility, upskilling. Education, technology. And I wanted to start my next business in a space that was really in touch with the workforce. And I think a lot of entrepreneurs overlook the world of associations. And as I spent more time talking to more folks, I just felt like I could spend at least another decade in this market.

[00:03:51] Uh, so that's how I met Amit. He was one of the first people I talked to in my exploration. And, uh, almost a year later, we are now [00:04:00] public with what we're building at Rally Board.

[00:04:02] Mallory: That's awesome. I was gonna say, it sounds like you and Amme have a lot of similarities. Uh, so it makes sense that your paths crossed, uh, what are you doing now, Jackson?

[00:04:11] Jackson: So I am the co-founder and CEO of rally board, which, uh, came out of stealth. Uh, initially in May this year, uh, we started, uh, really as I mentioned, by exploring the space of associations, uh, listening more than speaking for about 70 conversations with different association leaders. Uh, but principally we were interested in upskilling, uh, connection and member engagement.

[00:04:40] Uh, and so what Rally Board does today is it helps associations curate, uh, peer groups for every one of their members. Uh, engage those members in a cohort, and I'm sure I'll come back to this concept of cohort. Yeah. Uh, in their professional upskilling journey. Uh, and then provide [00:05:00] insights and analytics back to associations so that they can better support their membership and really enrich their data and visibility into the workforce they represent.

[00:05:08] Mallory: That is awesome. I'm sure we'll get a little bit more into that and what you've seen with the associations that you've worked with. But I really want to dig into this post that you made on LinkedIn, which is really what sparked our eye and made us think, okay, we've gotta bring Jackson onto the podcast.

[00:05:24] 'cause this is an incredibly interesting conversation for our audience. But you made a post comparing the Society for Human Resource Management, we'll call it SHRM, and the Josh Berson Academy. Uh, and kind of comparing, contrasting, and really making the argument the claim that perhaps the influencer market could be disrupting associations as we traditionally have known them.

[00:05:47] So I'm wondering what sparked you to make that post? How long have you been thinking in this direction?

[00:05:54] Jackson: I think there are a couple. Layers of exposure I have as a founder to this, this world. [00:06:00] Um, one is that many founders I know who are successful, uh, end up starting their second endeavor, uh, building a community that they ultimately monetize through some form.

[00:06:13] Uh, but. Most, on the most basic level, what they're providing to their community is content and connection. And as I've immersed myself more deeply into associations, there are just almost infinite number of parallels. Um, I think what is most different though is the lens that the founder or the CEO of these communities brings to their work.

[00:06:36] And you know, one of the examples I'm most familiar with because HR is adjacent to Ed Tech and my fiance, uh, has been a leader in hr, uh, is is Jasper Academy, which has actually been rebranded as Galileo Learn. But for those who don't know, Josh Bersin was an independent consultant in the HR space, became very well known, sold his practice to Deloitte, [00:07:00] and was effectively leading Deloitte's HR practice, uh, before retiring.

[00:07:05] The moment he retired, he started what he called Josh Berson Academy. It played a really important role in helping HR professionals sort of acclimate to the pandemic support teams in a very trying time. And as it's grown. From my perspective as an outsider, I don't know Josh personally. It seems to me to be increasingly competitive with H rm, which is itself an institution, it's hard to talk to an HR leader and, you know, not talk about HRM in the same sentence.

[00:07:32] Um, my post wasn't disputing the impact of H rm, but it was recognizing there is, uh, real competition brewing that I think is more tuned perhaps to the demands of, uh, millennial and probably Gen Z consumers of, of content.

[00:07:47] Mallory: Hmm. So, so interesting. So I went to the Josh Berson website and did some digging and research for this episode.

[00:07:54] And in the top nav bar you see membership. You see research, you see an annual [00:08:00] conference, a learning platform. Galileo learn a podcast. Then, uh, an AI assistant that he launched for HR professionals as well. With all that being said, it looks an awful lot like an association, but it's the Josh Berson, you know, business, LLC, whatever that may be.

[00:08:17] I, I wrote a blog yesterday, actually on the sidecar for the sidecar website and talked about the idea of building. Your own competitor as an exercise, kind of an entrepreneurial exercise for an association to do where if they were to start from scratch and am brought this up most recently, which kind of sparked the idea for me.

[00:08:36] But if they were to start from scratch, kind of none of their current governance and, and obstacles, what would they build? And in that blog I was thinking, you know, this is very theoretical. Surely there's not someone out there actively trying to disrupt associations. But I hadn't really thought about it from this angle, and so it's, this is really relevant for me and kind of ironic being that I just wrote this yesterday, but I want to dive into [00:09:00] three contrasts that you made in your post.

[00:09:03] One of them was that the Society of Human Resource Management, unbundled. Where be bundles? Uh, I'm curious if you can speak a little bit more to that.

[00:09:15] Jackson: Yeah, this is, you know, I'm not a pricing and packaging strategist. Um, I wouldn't say that this is the most fundamental difference, but I think what's, what's interesting is how, uh, JBA.

[00:09:29] Or Galileo is integrating what I see as the most valuable propositions an association can deliver into one subscription product. Um, I think they're probably playing into consumer expectations. Uh, they're probably recognizing that the purchasing decision is something that is a burden on consumers or.

[00:09:53] Uh, organizations and if that decision can only be made once, it's going to streamline and reduce friction. [00:10:00] So in this case, it's funny, when I wrote my post, I think it was like 20 something dollars a month. Mm-hmm. To get Galileo learned. Now it's almost $50 a month. So he's clearly increased his pricing.

[00:10:09] Um, but he's recognizing that for his particular product it's probably not a consumer paying, it's a director of HR going to their CHRO and asking for budget. And that's something you only wanna stick your neck out. Against once or twice a year, maybe you have a limited l and d budget you're tapping into.

[00:10:27] And I think it comes back to, you know, where associations get their funding. At the end of the day, it is a consumer paying for professional society, or it is an employer paying because they want advocacy or they want upskilling for their workforce. Uh, and you know, they're trying to price against that particular purchaser.

[00:10:45] And my guess is they believe a single subscription payment is gonna be more effective.

[00:10:51] Mallory: Hmm. And I guess, you know, being, well, they've up subscription prices and I, I mentioned this in my prerecorded intro, but Josh Burrs Academy [00:11:00] had reached one fifth of SHR M'S. Scale. At the point that you wrote this post, or I think it might have even been at the end of 2022, is when they had, uh, x amount of members that you mentioned.

[00:11:10] So obviously something seems to be working. In your opinion, do you think the association listeners in our audience should immediately run to, well, we should just bundle instead of unbundling, or do you think there's kind of some underlying current that perhaps that what works for Josh Berson maybe doesn't exactly work for associations, but maybe there's something they can learn from that?

[00:11:34] Jackson: I think there's absolutely something to learn. Um, my theory on competition is to ignore it as much as possible, even though I think humans are innately, uh, comparison driven. But I think comparison is the thief of joy for, for any, uh, nonprofit executive doing battle with these up upstart founders. Um, I think at the end of the day, uh, it's important to understand your customer.

[00:11:59] And [00:12:00] we call the members in the association world. Um, it might be the employer of the member, uh, but understand what they're looking to get out of a relationship with the association. And in some cases it could be unbundled. SHRM is still at a scale much larger than, than Josh Berson. Uh, and I imagine most incumbent associations have deeper ties and more practiced ways of pricing their, their products.

[00:12:25] And somebody might just want. A certification or a cert prep, they don't necessarily need the full experience. Um, but there's probably something to tap into there in terms of ease and convenience and, you know, knowing who. Josh Ian Targets in the HR market. It is a more, uh, innovation oriented, uh, professional, probably a mid career aspirational professional.

[00:12:49] There's a bit, a bit of a sex appeal to his brand as a non-HR professional, CEO of a startup with about a hundred employees. I was listening to his weekly HR podcast. I got [00:13:00] sucked in through that content. And maybe would've purchased his services for the HR team at my company, even though it was small.

[00:13:07] And I think it was very aspirational in its branding. And you know, simplifying pricing when you have a strong brand makes things easy.

[00:13:15] Mallory: Hmm, right. So it sounds like Josh Berson Academy, and again, my familiarity is, is really through your post and the little bit of research I've done, it sounds like they're nimble.

[00:13:25] They're moving like founders. There's more flexibility there. And there's also a great reduction in friction, which is something that we discuss a ton on this podcast. Like, your members go to you for some specific reason. Don't make them jump through 20 hoops to get that resource. Don't make them fill out a form that's 10 pages long to become a member.

[00:13:45] Um, something else that you talked about in that post was s is infrastructure. Berson is influence and then also sure operates by committee. Berson moves like a founder. I think that kind of goes back to what we've been saying thus far on the [00:14:00] podcast. I understand what you're saying, that comparison is the thief of joy.

[00:14:05] But I also can't help but think we have association leader listeners thinking, well, if we could just move like a startup, we could do all these things. If we could just, you know, limit our committee structure. We could do all these things and more, right? They have the trusted brand. They've been around for a long time.

[00:14:23] What, I guess, what is your advice to those people?

[00:14:27] Jackson: I think this is where there, there is an opportunity to learn, you know, I, I will not overstep and suggest I'm any sort of expert in association governance, uh, and wouldn't pretend to give the most effective advice on navigating that governance structure.

[00:14:43] But I think this is where there is a real threat. Because as I said before, at the end of the day, associations have to play to consumer and employer sentiment and buying expectations. And as you all have covered on 70 some episodes, you know, [00:15:00] AI is making it easier to build great products. Maybe great is a strong word, to build, uh, good enough or at least, uh, solid products.

[00:15:09] And, you know, through my, my founder lens, I think a lot about product versus distribution. You, you know, influence versus infrastructure is a good parallel to draw, uh, what influencers have, what creators have, what the celebrities of every corner of our economy have is distribution. They have followers, and Joss be, in his case, has a million LinkedIn followers.

[00:15:32] Um, that in some ways is more valuable than any product he can build. His products may be half as effective as shr m's. Uh, and influencers across the entire economy may be half as effective as the associations they're competing with, but what they have is this aspirational brand. They have thought leadership and you know, there is a brand behind the association, but people tend to lean into human relationships more.

[00:15:59] And I think [00:16:00] about what might happen if someone like Ryan Reynolds created a marketing association. He is fantastic at marketing and people, millions and millions of people watch every video and post he puts out onto social media. Um, he could have a very mediocre. Membership product. Uh, that includes events, uh, that includes content, whatever you want to incorporate into that product.

[00:16:23] But because it's Ryan Reynolds, people will purchase it. And that's, I think, what's happening with a lot of these creators. They have the distribution, it's becoming increasingly cheap, uh, using, you know, AI to coding tools, uh, you know, to whip up a website, create a minimum viable product, and start pushing it out to members.

[00:16:41] I think there's an entire ecosystem also of software that supports these, uh, these entrepreneurs. YouTube, uh, can be heavily monetized. Um, community platforms like Circle, Patreon, Substack, uh, there are reporters making enormous amounts of money just by posting to [00:17:00] Substack when they. Previously had to go through trusted institutions like the New York Times or Wall Street Journal.

[00:17:06] And so I think this is all part of the same paradigm shift where it's becoming increasingly easy to compete and those who have influence can build products relatively quickly, slap their brand on it and push it out to the consumer who is more attuned to their. Uh, their communication, their thought leadership, and I, and I do think that poses a real threat.

[00:17:27] We've been talking just about the HR space, um, but if you look across every industry, I wouldn't be surprised if there's somebody doing something similar with a paid community. They might not call it an association. They'd probably call it a paid community, but I would be shocked if it didn't exist in almost every corner of the economy.

[00:17:44] Mallory: This is good stuff. I think, as you mentioned, we talk about it a lot on the podcast. Knowledge is basically. A commodity, uh, or it will soon be. And so if that is what your association has been leaning on to create value, you're, you're positioned [00:18:00] to be disrupted as you talked about Jackson. But I think what's interesting about what you said is this idea of influence in community, especially in the age of ai.

[00:18:08] Something AI I hope will never do is, is cultivate human relationships in a really deep fashion and have that level of influence over us. I think Ryan Reynolds an excellent. I wanna do a brainstorm. Not that either of us have all the answers, but for an association that is, you know, steeped in tradition has always done things a certain way and it's worked out very well for them.

[00:18:33] Uh, up until this point, perhaps. How do you think they could go about cultivating influence distribution, that seemingly abstract like ethereal thing? In a way that's still unique to their association and kind of building on everything they've done in the past.

[00:18:55] Jackson: Yeah, I think there, you know, there's probably some [00:19:00] hesitance to partner with the likes of Josh Bersin's and the Ryan Reynolds of every industry.

[00:19:06] But I, I think this is a scenario where both parties have the same interests and the same mission. Um, and it's just a matter of organizing a collaboration that works, uh, for both. I, I suspect Jasper in today is still a dues paying member of SHRM because, uh, SH RM is while not as innovative in this line of of discussion is the trusted brand.

[00:19:35] And a 6-year-old startup founded by a trusted brand like Josh, even so doesn't have the tradition, which is itself a competitive asset of an association. Um, when HRM puts out policy, uh, when traditional associations put out their perspective, uh, it does carry weight and that itself is distribution. What they might lack is that sex [00:20:00] appeal of the upstart celebrity figure within their, their community.

[00:20:05] And I, I suspect there are ways to partner together to bring more people into the fold of an association to build more exciting products for members. And it doesn't have to be a competitive endeavor. So I think that's, that's probably where I would start if I was the CEO of an association and noticed somebody else sort of putting their hands up and, and creating sort of competitive events.

[00:20:26] I might try to partner. I think the second thing you know is to think about what competitive assets and association has relative to the, you know, upstart. And I think there are two, I mentioned one already, it's trust. Um, it's, uh, the fact that. There is a history of. Perhaps quality, um, and trust within the organization in terms of the content they put out, the certifications they put out.

[00:20:55] Um, and they probably have employer relationships where those certifications [00:21:00] and points of trust carry more weight. Uh, but the second is there's an existing network that's enormous and this is where my bias will come up. But, um, what rally board is building is fundamental to the social capital or the networks that associations are very rich with.

[00:21:17] Um, there might be decades of history of individuals coming to an event. Uh, they're loyal to that event, to that community. And when I look at some of these creators and the products they put out. Another one worth looking at, by the way, is Dave Gearhart in the marketing space. It's called Exit five.

[00:21:34] That's his paid community. And if you look at his website, the number one offering he has for CMOs and VPs of of marketing is a cohort. He is giving people access to a curated network that they can't otherwise find by going on LinkedIn and searching, by going on message boards and searching, they are bringing that network to you.

[00:21:54] And one of the reasons I wanted to partner with, with associations in the first place with rally board is that network is there [00:22:00] already. It's maybe not fully tapped. But the membership of an association is itself a wildly valuable asset that if curated effectively could be a real differentiator for an entrepreneur who's pushing out podcasts and great posts, but maybe doesn't have the trust or the, the coherence of a network that they could bring to bear.

[00:22:18] Mallory: Mm-hmm. I love that. The first thing you mentioned was collaboration and partnership. I don't know if maybe I'm, I'm working from a competitive mindset here, but immediately I'm thinking the association, you know, identifying an internal influencer that they have and, and trying to build that from scratch.

[00:22:34] What are your thoughts on, I think partnership's great, especially if there's someone willing to partner with you who's already done a lot of the legwork upfront. But what do you think about an association who says, well, why couldn't we. Do what Josh Berson has done. Why couldn't we, you know, be more active on YouTube and TikTok or you know, LinkedIn videos?

[00:22:55] Do you feel like that is a path they could try or do you think there's more value [00:23:00] there working with partnership?

[00:23:02] Jackson: I think every association should probably look inward and determine where their core competencies lie. And my guess is it's not gonna be content learning sponsorship, it's not gonna be everything.

[00:23:14] And I think there is a, a tradition from what I've seen so far of, of outsourcing and partnering with vendors to run things like events. I think the same can be said for distribution. Um, it's maybe a more novel theory of partnership to reach into the workforce in ways that that might not already be occurring.

[00:23:32] Um, but I think if I look back at the last industry, I, I worked in higher education. Uh, you had brands like Harvard. You see Berkeley partnering with for-profit companies to launch online learning degrees and short form courses that in some cases would net the institution tens of millions of dollars a year.

[00:23:51] Of course, they would not put that for-profit company's brand on the program they were launching. But when you think of places like Harvard with $30 billion [00:24:00] endowments, partnering with partners to deliver quality to their stakeholders, I think the same. Parallel can be drawn to associations. I think there's hubris sometimes when we think we can be good at everything.

[00:24:15] Mallory: Mm-hmm. I know

[00:24:15] Jackson: for my startup, uh, we are not building our own CRM for example. Yeah. Uh, we are not building a lot of tools. In fact, we have a very strong bias towards buying over building because we know there are very few things that we wanna make. Our core competency, our core competency in some ways is how can we move as fast as possible?

[00:24:32] Um. Make decisions quickly. I know that might be different from a nonprofit association, but I'm sure there are other areas of specialty that the association can lean into. And with the right partnership, you might immediately, you know, quintuple the reach, uh, quintuple, the non-dues revenue you can drive.

[00:24:53] Mallory: I think that's an excellent point. So you talked about the two unique assets that an association has being that [00:25:00] trust, that brand, that quality. And then also the network. And so I'm hoping you can talk a little bit about through your work at Rally Board working with associations, what success have you seen helping associations tap into one of their most valuable assets being their network?

[00:25:19] Jackson: Yeah, so just a brief description of, of what Rally board does. Um, we kind of think of our product as threefold. The first is curating a very large network into small sort of micro communities. We call them cohorts. Uh, because what we found is that after post-secondary education, uh, you don't really have a cohort in the workforce.

[00:25:44] Um. Maybe your first job has a class of new hires that start together and build some sort of bond on the job, but it gets increasingly lonely as you move deeper into the workforce. Not to mention, you know, we're facing a loneliness [00:26:00] crisis in this country. Um, and so what we're focused on, step one is across a membership base that might be 500,000 members giving every member access to a small group of five or 10 people who are most relevant.

[00:26:14] To their personal professional context. Now, that might be data pulled out of a MS. It might be a matching survey we send to members who wanna participate in these types of cohorts, but we're focused on highly curated AI driven matching to give people that that initial connection. This is modeled off of, uh, YPO.

[00:26:34] I know me, I think is a member of eo. These are common models for executives, uh, CEOs and founders who might pay quite a, a large sum of money to get a small curated network of other CEOs in a similar context. Um, I was part of one of these in my last job. It was amazing. It was life changing, but it was way too expensive to bring to my entire team.

[00:26:57] I looked for products that would allow me to bring that sort of [00:27:00] peer group to my, my team, and it just wasn't available. And I think associations have the capacity to deliver something perhaps for free as a member benefit or as a paid offering to their members. Um, and so what Rally Board does, first and foremost is create that small cohort.

[00:27:15] The second thing we do is drive ongoing engagement and learning. Um. Some, you know, associations might call this their signature program, which could be a leadership academy, and they, they do it already with an in-person offsite. Um, but it's constrained to a small number of their members who have the resources to pay or they have the resources to staff.

[00:27:37] What we envision is a much larger implementation of that type of programming. Um, other forms of this could be, you know, recurring round tables, uh, any forum in which people come together to talk about the issues that matter most to them. That is what Rally Board supports once these cohorts are formed.

[00:27:54] And then the third aspect is the insights that we can generate from this engagement. Uh, [00:28:00] it, it gives associations visibility into what their members are discussing and care most about so that they can inform their strategy. And so, you know, when I think about catalyzing the network of an association, it is creating the type of programming that they demand and desire.

[00:28:16] Um, I think this applies across young professionals who are lonely and struggling to onboard into their work. They're looking for their tribe, uh, and I think it applies just as much to executives who are lonely at the top. Looking for people who maybe, uh, are facing the same decision making challenges are in the same region, share the same affinity.

[00:28:36] Uh, there's a lot of race and gender based interest in these types of cohorts. I suspect across an industry, you could think of countless ways that you could match your members together for these types of discussions. Um, but the real power of, of what we're proposing is that stickiness of the cohort that keeps folks coming back, attending the annual conference where they can meet their cohort in person.

[00:28:58] Mallory: Wow. That's [00:29:00] incredible and, and hearing you talk about the cohort, I'm not sure if you're familiar, but something we've done at Sidecar is our AI mastermind group that's specifically for association CXOs. Perfect example. We need to have that cohort. And what's really interesting is one of the members of the AI Mastermind, and maybe more than one has actually launched that within their association, a cohort, but.

[00:29:20] It's impossible to do. I won't say impossible, but it's really difficult to do at scale without some sort of AI driven matching. I'm sure. Uh, I don't know if you can talk about any, you know, specific associations that you've worked with or had conversations with, but maybe generally, I know you mentioned there are lots of options with the cohort, but which one of those being like asynchronous learning or maybe in-person meetups at annual conferences, where have you seen some really promising early success?

[00:29:49] Jackson: So, uh, we are, you know, in the design partner phase with our early partners and I'll, I'll talk about a few at a high level, but without giving away specifics, given the work is, uh, in [00:30:00] flight. Um, so you know. There are, there are multiple models I've described. What, what, what we found to be most effective is, and what we're focused on strategically is synchronous engagement.

[00:30:12] Okay. So as opposed to a forum where people can post and respond. The primary modality where we're engaging is a Zoom call. Our app is a companion to. Zoom engagement. Uh, it allows people to structure discussion, to, uh, take takeaways from every discussion, uh, to nudge folks into certain ways of engaging together.

[00:30:36] Uh, but we are focused on live engagement. Now, in between the live engagement, there are ways a cohort can communicate, which we support, but we are really interested in how do you get eight people to show up, for example, to a Zoom call and engage in the most authentic way possible that. Gives them the most value possible.

[00:30:54] Um, so there are many different applications of that. But as an example, you know, we're working with Project Management Institute, [00:31:00] which is one of the largest professional associations. Um, I think it's over 700,000 members or so. And, you know, there are two applications for working with them. One is, you know, within their community team supporting the value inherent in membership.

[00:31:16] There are ways to, uh, create group mentoring sessions. There are ways to, uh, bring chapter leaders together around different topics. Uh, just to give you a brief flavor of the membership side, but then on the learning side, PMI, I didn't know this before, we engage with them, but they are a very impressive learning organization.

[00:31:35] They reach the scale that even the largest universities could barely dream of. And you know, they have a lot of online courses that are asynchronous. Watch a video, take a quiz, check for understanding, move to the next video. That is how most online learning occurs. But what if you could supplement that learning with human synchronous interaction, real connections in the workforce that's relevant to a cohort of people moving through a program.[00:32:00]

[00:32:00] That's the learning application for Rally board. Uh, and, and I'm sure there'll be many more applications for what we're doing that we'll discover through our early partnerships. Uh, suffice to say, uh, associations have a lot of places where people come together on video chat calls to engage, uh, and then they go back.

[00:32:18] And there are ways for us to automate all of that, uh, to enrich those interactions and bring it to many more members of the association.

[00:32:26] Mallory: I love that at the top of this episode, you mentioned your fiance congrats as well, um, and that they work in hr, which is kind of the lens that you think about these conversations through, which is interesting for me because I've mentioned on the podcast, my husband works in healthcare and so he's a member of.

[00:32:44] An association for a specialty and for his profession specifically. And so I'm always thinking about these conversations through that lens. And so I'm thinking the power of him as an early career healthcare provider, having a cohort, I'm not sure if his association does anything like that, which is why I won't mention [00:33:00] them by name.

[00:33:00] But having a cohort of other early career professionals that he could meet up with live synchronously, how powerful that be. And then tying also back to the beginning of the conversation, I know for a fact that he has watched. Influencers, you know, on YouTube, listen to their podcast in his profession. So, as you mentioned, Jackson, we might think it's farfetched to have, you know, in every corner of the earth, these people that are really pushing out influence and curating a network that are in direct competition with a lot most associations, most industries, most professions.

[00:33:34] So I want to. Talk a little bit about, for the association leader who is listening to this episode, feeling inspired, feeling like their minds opened a bit to this element of human connection and influence. If they do identify an influencer emerging in their space, for example, which is probably already happening, like you mentioned.

[00:33:57] What do you recommend that they do? I mean, besides kind [00:34:00] of watch it and take it in and and think, huh? Like, how could that disrupt our space? I know you talked about partnership, but kind of what are some tangible things they could bring into their next leadership meeting and discuss?

[00:34:13] Jackson: Yeah, I think, I mean, there's the collaboration versus competition discussion and you know.

[00:34:18] In some cases, maybe competition makes more sense than collaboration, but if I were them, I'd probably invite that influencer into a conversation. Um, I might explore if they're desiring some form of revenue share agreement where their content can be coupled with the association's trust, if they can build together, uh, to bring the, you know, associations.

[00:34:41] Trust and content into the influence of that individual. Uh, there's probably a lot of non-members consuming content, uh, of that individual and that. That could be a base of, of marketing for the association. Um, but then I think there's, there's more tactical [00:35:00] discussions around what sort of product that could, could be brought into the market together.

[00:35:06] Um, associations, you know, might be interested in launching something like a peer group with, with an influencer, even at a micro scale as, as sort of a testing ground. Um. A lot of the most effective executive peer groups I've been a part of have a facilitator. Maybe this influencer or members of their organization might want to be facilitators for a paid product that could be brought to the leadership of an association's members.

[00:35:31] Um, you know, there's so many ideas of how to collaborate together, but I think what I'd want associations to recognize is that these creators have made it their, their livelihood of attracting followers. A subscriber base, maybe that subscriber base doesn't pay, but they're generating income for the creator through ads, through platforms like Instagram, LinkedIn, YouTube, et cetera.

[00:35:53] And ultimately, when people get to a certain level, they're looking for ways to monetize that community. Now, [00:36:00] I know we don't use that word in associations monetizing, uh, but the reality is that that's what it means when you build new products and bring it into, into the member base. And, uh, I could expect.

[00:36:12] Them to be interested in bringing a shared product offering to their, to their member base that might even convert folks into being longstanding members of the association. Uh, I think at the end of the day, everyone probably has the same mission, which is to support the membership of the association to advance their interests, whether it's healthcare, education, manufacturing, like we're all in it together.

[00:36:32] That's my perspective and I'd, I'd start with that collaborative conversation.

[00:36:36] Mallory: Hmm. I love that. At the end of the day, you have the same mission, whether that's partnership, maybe it's competition in the end, but you do have the same mission. You ended this infamous LinkedIn post, which everybody should check out, and we'll link in the show notes by saying, the future of professional learning won't be owned, it will be earned.

[00:36:55] What do you think earning professional learning is going to look like? [00:37:00] I won't go too far. 10 years is too far away for now, but in the next few years, what do you think that looks like?

[00:37:06] Jackson: Yeah, I think it comes back to something you alluded to, just the idea that information and knowledge will be increasingly commoditized, and so there's a lot of free content.

[00:37:17] You can go to YouTube and probably learn something about anything. You can go to Reddit and probably find a subreddit that is specific to your, your area of, of interest. And those are all, whether they say it or not, competing products relative to what associations provide. And so, you know, associations like it or not have to compete with universities.

[00:37:38] They have to compete with influencers, with learning platforms like Coursera. And there's going to just be more and more information that is trying to monopolize our attention. Why? One of the reasons I believe so deeply in rally board is that, um, what will be increasingly scarce is real. Authentic relationships and connection.

[00:37:59] [00:38:00] Not responding to somebody on a LinkedIn post in the comments, not even posting to Reddit, but the human relationships that so many associations find at their annual event. And when I spoke to members of associations and CEOs of associations in my discovery work for Rally board, that was the thing that lit up everybody's face is like people know the value when they see it in person at the event.

[00:38:23] Getting people to the event is challenging. Not everyone can make it and it only happens a couple times a year. So what is there in the intermediary time to create that authentic human relationship? Um, that's where I would wanna focus in terms of differentiating myself over the long haul. It's gonna be really hard to compete on content because anybody can create it.

[00:38:44] You don't even have to have a paid chat GPT account to go create some content, and it's only gonna get cheaper. But content plus real connection, that'll, that'll be special. And associations have the network, they have the trust. How do you lean into creating that connection as your long [00:39:00] differentiator?

[00:39:02] Mallory: Ooh. That was a good mic drop moment content plus real connection. And I would argue that associations are in no better position than, than to leverage both of those things really effectively. Uh, I think the idea of leaning into human relationships in the age of I AI is essential. And we talk about digital now a lot on this podcast.

[00:39:23] Jackson, I don't know if you've ever been to Digital Now, which has already Little bit. I

[00:39:26] Jackson: haven't, but I, I plan to be there before long.

[00:39:28] Mallory: Yeah, absolutely. We would love to have you there, but there is something magical about in-person connection like we can do. Yeah, I mean zoom, zoom is a lot better than asynchronous as well, but getting people together and feeling the excitement, feeling the energy, that is something.

[00:39:46] That I hope AI will never be able to replicate. And so I agree with you, I think that's a place that associations can lean into in the next few years as content becomes cheap and easy to make. And to your point, Jackson, the [00:40:00] association still might have the best content in their space, in their profession and industry, but the fact is, if somebody has more influence, maybe a half as good product does even better than yours.

[00:40:11] Um, so I wanna thank you so much for being on the podcast today. This. Conversation was really insightful for me and I hope very helpful for our listeners, where can people learn more about Rally Board if they want to get info on that, and where can they keep some tabs on you?

[00:40:29] Jackson: They can go to rally board.com if they wanna check out our website, and I'd encourage them to connect with me on LinkedIn.

[00:40:36] We are at the, in my experience, the most fun stages of company building where we're really building with. Not for our customers. Um, so we've been quite careful about who we take on as early partners and uh, we have big aspirations with those early customers. But, um, we will be opening the door a little bit further over time as we more deeply validate what Rally Board has built.[00:41:00]

[00:41:00] Uh, and we're kind of in that stage now. So would love to hear from you. And, uh, it's just been a joy to spend more time with associations. It's probably the coolest industry I've been a part of.

[00:41:11] Mallory: Oh, well, I agree with that. It's the coolest industry I've been a part of too. Jackson, thank you so much for joining us on the Sidecar Sync Podcast.

[00:41:19] Amith: Thanks for having me. Thanks for tuning into the Sidecar Sync Podcast. If you want to dive deeper into anything mentioned in this episode, please check out the links in our show notes. And if you're looking for more. In depth AI education for you, your entire team or your members head to sidecar ai.