Beyond the Tech Stack: How AI Is Changing the Association Playbook
In this episode of Associations NOW Presents, recorded live at ASAE’s Annual Meeting & Exposition in Indianapolis, host Sharon Pare welcomes Ronald McGrath, owner of High Road, for a conversation about the rapidly evolving technology landscape and what it means for associations. McGrath shares his perspective on the growing importance of artificial intelligence, why associations should embrace experimentation rather than wait for the perfect solution, and how AI can enhance everything from member engagement to everyday operations. Drawing on decades of experience developing technology solutions, he discusses using data to better understand member needs, personalize experiences at scale, and make smarter decisions about products and services. The conversation also explores how associations can connect their existing technology systems, balance automation with human judgment, and leverage emerging tools to work more efficiently while creating greater value for members. Check out the video podcast here: https://youtu.be/CxLFhZVLWro This episode is sponsored by Highroad Solutions. Associations NOW Presents is produced by Association Briefings. Transcript Sharon Pare: [00:00:00] Welcome to this episode of Associations NOW Presents, an original podcast series from the American Society of Association Executives. I'm Sharon Pare, partnerships director at HighRoad Solutions, a HubSpot agency. Today, we're recording from the Super Bowl of association events in Indianapolis, and today, this episode is sponsored by HighRoad Solutions. I am so excited to interview the owner of HighRoad Solutions, somebody I've been working with for five years and have admired in the space in the decade that I've been in the industry, Mr. Ronald McGrath. Thank you so much for joining us today. Ron McGrath: Thank you for having me. Sharon Pare: So Ron, today we're gonna talk about AI and where associations are headed, but I actually wanna start with you. You've spent a lot of your career seeing technology shifts coming, sometimes before the rest of us have seen them ourselves. But before we get into it, I know you've been on the floor for the past few days, Saturday, [00:01:00] Sunday, now we're into Monday, and you've met with a lot of our prospects and our clients. So what are you hearing on the floor right now that you wanna share with our listeners today? Ron McGrath: It's an exciting time. A lot of cool things going on with technology. A lot of people looking at their technology stack and trying to figure out how to upgrade it. Also learned from one of the keynotes that we're bad at lying. Our body tells the truth all the time. And so the O's is how you say his name. That was pretty phenomenal. And that the '80s wouldn't have been anything without Babyface. Sharon Pare: Let's go to Babyface. I know you made it just in time. Yes. You landed just to get to Babyface. What was your favorite performance of his that night? Ron McGrath: So first of all, I was impressed that he's 68 and looks as good, and he can move as well as he can. Sharon Pare: Yep. Ron McGrath: But also, I didn't realize that he was involved with Bobby Brown when he broke off of a new edition with Don't Be Cruel, Every Little Step, and so just touched so many artists. So it was a lot of fun. I know people said it was hot, but that was great. And then the drones. After he [00:02:00] finished and you turn around, and then you see up in the sky, "Welcome ASAE to Indy," that was amazing. Sharon Pare: So speaking of the drones, and before we get into HighRoad, I know you've always been a developer at heart, like getting into that tech stuff. Where does that fascination with building things and figuring out the next techno- technology come from? Where does that come from, that Ron the builder? Ron McGrath: Oh, what is it? Good questions. I used to get... So when I was a kid, I used to have these kits. My mom and dad used to buy me these RadioShack kits. It's like a 50 in one, so you could wire them together, right? Like an FM broadcast tool. So I was always kind of into gadgets. I had these Tinker Toys. And then I actually had computers, like one of the first computers, a Timex Sinclair, a Commodore VIC-20, a Commodore 64, an Amiga. So I always played with things, just always curious. I also- Would take things apart and not always put them back together, so- Yep ... I was a thorn in my dad's side a little bit. But looking back now, that's part of why I'm a tinkerer, and that's kind of what you gotta do. Roll your sleeves up, play with things, not- don't be afraid of [00:03:00] technology. Sharon Pare: So obviously you love innovation, you love trying the newest thing, but associations can't always chase that shiny object that comes along. So how do you know when something is actually worth paying attention to for an association? Ron McGrath: Oh, that's a good question. Yeah, 'cause there's a lot of hype a lot of times when things come out. Obviously, AI I don't think is over-hyped, honestly. But then you have, what, crypto before that and stuff. So I think it's hard, because nobody can predict the future. But, and typically the thing that actually does get traction is the thing that we don't expect. But I do think right now in this time, AI really is getting traction more so than other things. But yeah, it's kinda hard to say what's gonna get traction most of the time, I think, yeah. Sharon Pare: So why don't we go way back. So before Highroad was Highroad, you were in the fax business. And we're not talking a few faxes. There were millions a month that you guys were sending. So when did you realize, okay, this is changing and we need to move to email? [00:04:00] Ron McGrath: So first of all, that's where I met Dave Trusso. And at first I was shocked that people paid that kind of money to send tens of thousands of faxes. So that was the first thing. I was like, "Okay, how do you even do that?" But I think the honest answer is I didn't know, because I remember the CEO of that company, his name was Sanjiv Maloney, really brilliant guy. R- he's an engineer by trade, really articulate. And I remember he had built a new service called Certified Email, and this is before all the email providers. And I remember going out to a big customer to pitch, and he called me into his office. He said, "Look, Ron, I need you to show this." And he's like, "This is called certified email. You have to show this." And I'm like, in my head I was like, "No one's gonna pay to send emails." Right? And so obviously he had some vision into it, and we showed it. It wasn't something that they would buy right then, but it was more of showing them what the future could be, and that in itself really closed the deal. So yeah, the fax stuff, it was [00:05:00] important at that time. Didn't know what the next thing would be. Certified email was the precursor to actually people wanting to do more and more email, and then you had all the other companies develop after that, so. Sharon Pare: Now we've lived through fax, went to email, now email to marketing automation, and now marketing automation to AI. So are we sitting in one of those other moments we're not, we're, we're not really sure yet? Or what do you think about that? Ron McGrath: I think marketing automation and omni-channel and being able to touch and meet customers on the channels that they prefer, that's here. What the new channel's gonna be, who knows what the next one's gonna be. Apparently, when us older people get on certain channels, the younger people wanna move to the next channel. So you're gonna have that and tools that support that. They're gonna add those new channels. But the fundamentals of marketing are really the same, it's just the channels you meet 'em on. I think AI is an, a kind of a force mul- multiplier that can sit under all tech stacks, not just marketing, and I think you're gonna see huge ... I think we're at an inflection [00:06:00] point with AI. Mm. That it's not the AI that's gonna replace you, it's someone that uses AI better than you do, and that's the thing that I'm trying to get the people that I care about around me to focus on, make sure that they're using it as a force multiplier. Sharon Pare: So let's dig deeper into that. HighRoad is now an AI-led company, especially with what we're building on top of Hub- HubSpot. For an as- association that wants to get started without six months of committees and red tape, what is one thing that they can start doing tomorrow? Ron McGrath: So I think ... That's a great question. So I feel like there's this, been this evolution. We've talked internally, and when I share things they're not necessarily my ideas. You just catch ideas. You don't really create ideas, 'cause it's a culmination. It's a community. It's like associations. So one of the things that we've been batting around is this evolution back to the command line. So when computers first started, the way you interacted with them wasn't through a mouse and through Windows. It was actually you would go to a command line, you would type some things in, but you had to speak the language of the computer And then you had the UI with the mouse, and so you're interacting in a visual way, something that's more a [00:07:00] metaphor, that's more something that a human brain can understand. And then Google kind of re- reintroduced the command line through search, and now we're back to the command line. But the difference is we're not speaking the language of the computer, we're speaking the language of the human, and it understands us. So the reason I give that foundation piece is when people are thinking about AI, you, you don't have to be a prompt engineer. Yes, there's a, there's a kind of a methodology to it, but really you just talk the way you would normally talk to a coworker. That's the beauty of AI, so everyone can do it. I think there's sometimes a little bit of fear because I think the initial thing that came out was around some of the bad actors that could leverage it to be better at being bad actors. But don't let that hold you back, because really the only way you're gonna really kind of understand it, it's like ice cream. It's like I could explain it to you. I could be a noble laureate, I could be a poet. I could use a thousand words, but until you have ice cream, you won't know what it is. So you've gotta get out there, get your hands dirty, play with it. Don't feel like, be like me with my dad. Break something. Don't put it back together. Just play around with it. [00:08:00] You'll understand it for yourself. Sharon Pare: You just mentioned something and you're, I've noticed you're wearing a pin today. It's YDKWYDK. What does that mean? Ron McGrath: You know what it means. You gave it to me. I did. You don't know what you don't know, but I love that phrase. It's a good phrase. It's true. Sharon Pare: So speaking of fear, what do you think right now is the hardest truth that associations are facing right now? Ron McGrath: In terms as an association? As an association. I think it goes back to what Reggie has been saying for years, understanding their members better, really tapping into the signals that you're getting, because we should know that. We should know more about what your members want just based on the signals they're already giving off behaviorally, and also being able to ask them kind of questions, too. But really picking up on those signals and making sure that you're serving them in the right way, and it's not like you can serve all members in the same way, right? It's gotta be personalization at scale, like understanding what is important to each individual member. You might have 10 member benefits. These three might resonate with member A and another four [00:09:00] might with member B, so just zeroing in on that and having data to drive those experiences. Sharon Pare: Speaking of the data, speaking of Reggie Henry, I think there's something that resonates with a lot of us in the space around that system of record and then the system of action. Can we dig into that a little bit more, what that exactly means for an association? Ron McGrath: Yeah, so I think a big thing that we champion is getting tools to play and work well together to create more value overall. So where we have developed that term is m- most associations use an AMS to manage the business of an association. You're gonna continue to do that. You're gonna continue to need to do that. And then what we do is we implement HubSpot, right? We implement it, and we integrate it for associations, and our integration product allows the AMS to can still be the system of record, but then HubSpot becomes their system of action, their engagement layer, where they'll be able to look and understand their member better, because it's picking up on all that digital exhaust and signals. So system of record, system of action, each one of the [00:10:00] platforms make each other better, which creates a better experience for your member or prospective member. Ad Read: Let's take a quick break for a word from our sponsor. HighRoad helps associations turn their data, campaigns, and strategies into action. As a HubSpot Diamond partner built specifically for associations, Highroad helps teams connect their systems, better understand their members, and create smarter, more personalized experience and operations at scale. Whether you're exploring AI, seeking models that turn data into currency, augmenting your sales and marketing strategy, or simply looking to create efficiencies within your organization, HighRoad helps you move forward with clarity, confidence, and a plan. Sharon Pare: I wanted to go back to the last question, and we're starting to talk about some of the hardest truths that the associations are facing right now, and go into that data a little bit more. What happens when the data tells you people simply don't want what you're offering? Ron McGrath: Yeah. Sharon Pare: I know [00:11:00] you've heard it before. You've talked about it- Yeah ... before with some of our Highroad clients and prospects. Yeah. But tell us about that. Ron McGrath: So I've been meeting with several association CEOs, and they really want to continue to leverage data to tell a data story, to be able to kind of champion things within the organization. And several of them have come to me and said, "Hey, look, it's not always the marketing." Things get pushed onto the marketing in terms of, okay, these campaigns aren't driving what we want. But what they're really looking for is being able to say, "Okay, what can we do to improve our marketing? But also, what is this telling us about our product offering in general?" Sometimes people just don't want what you're selling. Sometimes it's better not to resist that idea because the longer you're in resistance, the longer you're away from actually moving in the direction that's aligned to what the customer's basically saying that they want. Sharon Pare: All right. How do you help a team that's nervous about AI actually get on board without pretending the concerns aren't real? Ron McGrath: Yeah, I think, so it's [00:12:00] funny, there are all these interviews. There's the guy, forget his name, is father of AI. The neural networks guy, and he did a bunch of interviews talking about the dangers of AI, and I'm not saying it's not the AI, it's the actors, good actors- Mm ... bad actors. So someone asked in the interview, "So if it's so dangerous, why even release it?" He's like, "The upside's so much greater than the downside, you can't resist it." And so it's all about how it's being utilized. I think that you should be deliberate, and you should have and be intentional and think about those things, 'cause you have to be aware of data and those kinds of things. But at the same time, it's going at such a rate, not getting on board now puts you further behind, and that's gonna be... It's actually gonna give you as an individual, again, you will be able to outperform someone who's not using AI. It's gonna create better work-life balance, right? A lot of us have to work in the evenings just to keep up with the administrative things we couldn't do during the day. So I like to think of it as you have your own personal administrative assistant. It's not [00:13:00] to replace you, although some people could try to use it that way. The way that I see it and the way that we're wanting to leverage it at HighRoad is to improve the quality of life, to allow everyone to have an assistant so that those administrative things, you can get the AI to do that, and then you can focus on the higher level thinking. And even with that, it helps you with that, but you still have to be the domain level expert. You're still the one who has to translate this and communicate with the customer. So the way we're leveraging it is it allows us to understand our customer better. It allows us to create a much more personalized experience. For example, presentations. It's nice to have that as a way, as a communication mechanism, but there's not always enough time to do that for every situation. With AI, we can do a custom presentation from a transcript within two, three minutes. So it allows us to serve our customer better, right? I think definitely take those things for each organization. They have to look at them, those things themselves and make a decision. But don't let that get in the way to create too much hesitation, 'cause it's going to... You're gonna get behind, [00:14:00] and it's just moving. What AI couldn't do a week ago, it can do today. I just encourage people to get in there, experience it for yourself so you can form your own opinions. Don't rely on my opinion, on other people's interviews. Go there, use it for yourself. Form your own first party opinion about what it can and can't do for you. Sharon Pare: So with all the adva- advancements in AI and how much it's changing even over the past week, even probably in the last 30 minutes that we've, you know- Yeah been here sitting down- Tell me a little bit more about the human in the loop in the equation of AI. Ron McGrath: Yeah. So I, the way I still see it is you've got the chat interface and you have agents, but you really are, you still need a domain area expert to drive it. So for example, we might... So one of my friends came to me the other day and said, "Hey, look, I gotta review this new employee contract," and he realized he could use AI, and I'm like, "That's great, but don't not show it to a lawyer." Let's remove four or five cycles so that you're maybe not using as much billable hours with the lawyer, but make sure before [00:15:00] you actually sign something, you wanna have a actual lawyer look at it. But it accelerate, it's an accelerator. It allows you to move faster. It allows you to spend less money. That's a good example of an application. We're AI first. We're using it really heavily, and it's basically helping us as a company, helping us with our individual team members, again, creating better work-life balance, allowing us to be more productive, create better experiences for our customers. And so I'm looking at... But I'm a half full kinda guy, right? And that's why I have great people around me that say, "Hey, Ron, you might not be looking at something," because I'm ov- I'm an optimistic person. But I would say optimism is more in line with reality than pessimism, 'cause we take a lot for granted. More things go right than things go wrong. A million things went right today at ASAE Annual. Maybe one thing didn't happen the way you thought it should happen, so more things go right than go wrong. So I think optimism's more aligned to realism than pess- pessimism. Sharon Pare: So this is actually the perfect segue, because you talk about, a [00:16:00] lot about awareness, and I'm curious about somebody who moves really fast. When you're in full hustle mode, and we're bringing it down, we're bringing it back to Ron, right? For somebody who's in full hustle mode, where do you find that balance between that, that awareness and that, the hustle mode? Ron McGrath: Yeah. Now you're, now you're talking my language. So the first thing I do is this. I breathe. You won't believe what a breath will do for you. And so I do think that's kind of the foundation, definitely for us as a company, but I think each person has to find their place. But I think it's really important to stop and slow down. We're constantly inside our head thinking, and really that's not the place of innovation, 'cause you're really recycling the past. To get to a place of innovation, you've gotta clear your mind. Sharon Pare: Yeah. Ron McGrath: And then you get these lightweight lightning flash, lightning flash type insights, right? And I think definitely being more self-aware is helpful. It allows you to work in a place of innovation so you're not constantly repeating patterns. And then it creates space [00:17:00] between your stimulus coming in triggering you and how you react, right? You wanna respond and not react. So I think that's a critical thing, and I think the AI can help with that because it doesn't really have a skin in the game. If you ask it something, it's gonna give you an objective answer. Right. And sometimes it might not be the answer you want, but it might be the answer you need. Sharon Pare: Say that one more time. Ron McGrath: Might not be the answer you want , it might be the answer you need. I'm Sharon Pare: tracking this in my mind, too. Ron McGrath: There you go. Sharon Pare: So one of my last questions, I, is I wanna leave association leaders with one thing to carry home from Indianapolis. So five years from now, what is the decision you hope association leaders make today that they'll be grateful for? Five years from now. Ron McGrath: Five years from now. Keep doing what they're doing in terms of the community, and how we support each other, and how we're there for each other, and the important work they do. Because this is really, at the end of the day, technology's an enabler for solving people problem, not technology problems. And then again, just with the AI stuff, absolutely get on board, start [00:18:00] using it, set up a Claude account, a ChatGPT, Copilot. If you do it at work, do it at work. If not, do it personally. Make sure you don't get left behind of what's actually happening right now. Sharon Pare: Awesome. Thank you so much for those words. I wanna get to know Ron a little bit more, so I have a few questions for you that I wanna ask. So first question, what is something people would be surprised to learn about you? Ron McGrath: I can salsa dance. Okay. I can salsa dance. Bachata's my jam. Sharon Pare: All right. Ron McGrath: Dominican style. Sharon Pare: Didn't know that. What is one piece of advice you've received that has stuck with you? Ron McGrath: You are not your thoughts, you are the awareness behind the thought. Sharon Pare: This is an interesting one. If you weren't working in technology, what would you be doing? Ron McGrath: I'd probably be a philosopher if I could get paid for doing it. Sharon Pare: You did get some thoughts out today. And then last thing is, what is one thing on your bucket list that you still haven't crossed off? [00:19:00] Ron McGrath: Bucket list, huh? I won't use bu- bucket list. That's a good question. It's probably an experience. It's, that's not a, I don't really have a bucket list thing. Sharon Pare: That's okay. Ron McGrath: Good friend of mine, her daughter is very brave, and she just jumped out of a plane. And that is not something that I would normally do, but I actually had the seedling of a thought that it looked pretty free and liberating. And I'm not an adrenaline jun- junkie, and I'm actually kind of risk adverse. Interesting that I'm an entrepreneur in that way. But I don't know. We'll have to see. You'll have to come back to me. Maybe that might be it. Maybe that might be it. But that's the problem. I don't want the bucket list thing to actually kick the bucket. You know what I mean? That's right. Like, parachute doesn't open, something like that. Sharon Pare: Oh, terrible. Ron McGrath: So, yeah. So I'll have to, I'll think about that. Sharon Pare: We'll report back on the next podcast, yeah. Awesome. Ron, thank you so much for being our guest today on this podcast. Thank you for having me. It's an honor. [00:20:00] It's a pleasure. And thank you to everyone for listening to this episode of Associations NOW Presents: Industry Partners Series. Please make sure to join us each month as we explore key topics relevant to association professionals, discuss the challenges and opportunities in the field today, and highlight the significant impact associations have on the economy, the US, and the world. We want to give a big thanks to our episode sponsor, HighRoad Solutions, and be sure to subscribe to your podcast on Apple, Spotify, or wherever you listen to your favorite podcasts.
