See show notes for this episode: S 02 | Ep .. Aaron Dun.
0:00:00 - Alex Shevelenko
Welcome to Experience-focused Leaders! I'm delighted to introduce you to Aaron Dun, VP of Marketing at Thoropass. He is a go-to-market leader with 15 years of experience in growth product marketing—CMO, VP of Marketing, demand generation—you name it. He led teams at Datto and SnapApp, one of the pioneers of interactive content. He is also one of the top 50 CMOs to follow on Pavilion's list from last year. Welcome to the pod, Aaron!
0:00:33 - Aaron Dun
Hey, Alex, great to see you again!
0:00:36 - Alex Shevelenko
It's been a while, Aaron. Let's start with why we first connected. You were a marketing leader at a company called SnapApp, which ultimately got acquired and is now part of a company called PathFactory. You were at the forefront of understanding what it takes to create interactive content, and I really appreciated your thought leadership on that.
Let’s dive into it—what were the challenges around interactive content 10 years ago, and do you think they’ve changed?
0:01:18 - Aaron Dun
Right.
0:01:19 - Alex Shevelenko
In terms of B2B marketing.
0:01:21 - Aaron Dun
Yeah, well, thanks for the walk down memory lane. I definitely feel old now, Alex.
0:01:25 - Alex Shevelenko
Distinguished.
0:01:27 - Aaron Dun
Distinguished—yeah, that’s a better way of putting it.
You know, when you and I first met, I think it was at a MarketingProfs conference. You were a regular speaker and, honestly, a bit of a celebrity.
At the time, the core challenge of interactive content was that so much content was being produced as boring PDFs. Companies would ask people to download them and hope they became leads. The function of content had shifted toward generating outcomes rather than delivering real experiences.
What we found was that presenting content in a more interactive way led to greater engagement—people interacted with it differently than they would with a static PDF. I think we even had a graphic at one point with a PDF logo and a big red slash through it, like, let’s do away with PDFs!
But, you know, PDFs were the standard at the time. People knew how to create them, but buyers and prospects would often download them and never actually read them. So the question was: Can we create a more dynamic experience with that content?
Candidly, I think we gained strong early traction. Companies like SnapApp—and others at the time—were driving some really interesting insights. But it was a major shift for marketers. They were used to producing white papers, but creating them in an interactive way was a whole different challenge.
0:03:06 - Alex Shevelenko
So, essentially, you pinpointed the problem really well. But marketers—at least B2B marketers of that era—weren't necessarily ready to scale this solution. In retrospect, you were a bit early to market. None of the companies working on this at the time really made it to unicorn status from that first wave.
0:03:35 - Aaron Dun
I think there were a lot of great ideas and strong technology being developed. SnapApp was one of the companies that gained real traction. Full credit to the team—Seth and Russell did an amazing job building that business.
But scaling it to the next level was the real challenge. And honestly, fast forward to today, the problem still exists. The way people consume content has changed—we’re now in the era of TikTok (at least until the U.S. decides what to do about it).
0:04:17 - Alex Shevelenko
Even without TikTok, you still have YouTube Shorts, which pull people in the same way. Maybe the algorithm isn’t quite as strong, but the attention span issue remains.
And, as we were discussing earlier, thanks to generative AI, the volume of content has exploded. Even mediocre-quality content is improving. Now, people who previously had no business creating content are flooding the space with it.
So we’re heading into a storm: engaging people with meaningful content is becoming harder because competition is fiercer, and mindshare is being drawn toward more compelling, typically B2C media rather than B2B.
If you don’t mind, I’m going to quote you from that era and see what still holds true today. You said:
"Marketers are looking at how they can bring interactive content to their audience. It’s shifting from a static PDF—just a one-way push of information—to a two-way, engaged conversation with prospects. Marketers can share something of value, learn something of value, and use that information to identify who is ready to talk to sales now and who isn’t quite there yet."
That still holds up, right? Not much has changed in that regard.
0:06:06 - Aaron Dun
I think that problem still exists. The nuance and context around it, however, have changed exponentially.
We were joking earlier about how we’re on the cusp of an explosion in content creation—but we said the same thing five years ago. We said the same thing ten years ago. What has changed are the types of content being produced and the way people consume it. Attention spans have shifted as well.
At the same time, the opportunity cost of creating content has had the opposite effect. It’s lower than ever before. So now, we’re standing at the edge of another major shift. I’m not breaking any news here, but today, anyone can create content. Anyone can use AI tools to produce pretty good content. Right now, that sounds amazing—AI can help people generate high-quality content faster than ever.
However, history suggests we’ll likely see the opposite effect. A flood of people who don’t truly understand what content is supposed to do—how it should move the conversation forward—will rely on AI to churn out content. They’ll look at the AI-generated results and say, Eh, good enough. And sure, it’ll be far better than what we could have created ten years ago.
That means the baseline quality of content in the market will rise. But for content marketers and marketing teams, the real challenge is to go beyond that—to use AI tools strategically and create something truly engaging.
0:07:41 - Alex Shevelenko
Yes, and that’s the key word here: experience. What are your thoughts on that?
It seems like content is becoming more of a commodity, especially when it comes to images. Anyone can generate an image now. Video is getting there, but not quite—eventually, it will improve. But let's be honest: no one is going to sit through two hours of AI-generated video without, well… losing their mind.
So for now, content will still be mostly copy-based. And where does that copy end up? In something like a PDF or a blog post—just more of the same.
That’s why I liked your earlier quote—it really emphasized two-way engagement. And that’s where most Gen AI tools fall short, at least in how marketers are using them. They generate content, marketers clean it up, package it, and publish it—but AI doesn’t know whether it actually worked.
Marketers typically rely on entirely different tools to measure effectiveness. And because of that disconnect, content marketers don’t always get the credit they deserve for the impact of their work.
0:09:02 - Aaron Dun
The channels haven’t changed.
0:09:04 - Alex Shevelenko
Yeah, the channels are similar, right? So what do you think the key levers are?
At RELAYTO, we believe that experience is the message. People are drawn to experiences, but in this day and age, that experience needs to build trust. In a strange way, a structured document feels far more trustworthy to me than an AI-generated LinkedIn post that lacks credibility and feels like something everyone is doing.
A well-structured document carries a sense of authority. It can still be conversational—I don’t have to go through it page by page, struggling to read it on my phone—but it retains an element of credibility. I can glance at a summary, gain insights, and feel like there’s real substance there.
What’s your take on that—on the experience of credibility?
0:10:08 - Aaron Dun
I think you’re onto something important. When AI can generate good—or at least good enough—content, and when agents and bots are interacting with other agents and bots, trust becomes harder to establish. What does credibility even look like in that context?
We’re already seeing this play out in society. Not to get into politics, but here in America, people operate with different sets of facts and take action based on those differences. That isn’t new—it’s been happening since the days of town criers. But today, the speed and scale at which content spreads have changed everything.
In a B2B context, that challenge is compounded by the fact that the main distribution channels haven’t changed all that much. We still have LinkedIn posts, blogs, PDFs, websites. Sure, we now have podcasts at scale, TikTok, Reels—new mediums—but at the end of the day, content is still being pushed out in a format where people can only react to it after the fact.
We haven’t yet figured out how to make content consumption a true two-way conversation in real time. Adding live chat or chatbots to websites helps, but until we rethink the entire model of communication and interaction—the way early interactive content providers originally attempted to—we’re still operating within the same constraints.
0:11:51 - Alex Shevelenko
You’re still dealing with a one-way dialogue, even though you’ve made some adjustments around the edges.
Let’s talk about that, because the insight we gained from looking at interactive content historically is that it started as a marketing innovation. It was primarily designed for two target audiences—marketers and designers. Unfortunately, it remained outside of the website ecosystem.
But here’s the challenge: marketers aren’t necessarily world-class experts in interaction. Who are the experts in interaction? Sellers. Maybe even teachers using the Socratic method. The issue is that marketers are more focused on delivering a controlled storytelling experience—maybe with a Q&A at the end, but still a largely structured format.
One of the quirks of fate when we were building RELAYTO was that we had both marketers and teams handling high-stakes sales as customers. Sometimes, these sales teams worked with marketers—often called opportunity-based or account-based marketers—who supported conversations when salespeople weren’t in the room.
These teams drove certain features, but their focus was different. Instead of just pushing out content, they wanted to create engaging, non-linear journeys—more like an interactive discussion. A great conversation might start with: Here’s our agenda, but we have three different directions we could explore. Where do you want to dive in? The user then chooses, and the discussion follows that path.
So there’s a feedback loop, but it’s not completely random like ChatGPT. Sure, we offer that level of open-ended interaction, but it has its own unpredictability. Instead, you could design an experience that feels more intentional—something like: If you’re in this type of company, these are the three most common challenges. Which one do you want to explore today?
That approach feels authentic. It gives users control without overwhelming them. They’re choosing their own adventure, but they don’t have to overthink it or read through excessive content.
We experimented with this, but it didn’t scale well. The issue was that it required moving beyond the traditional PDF or PowerPoint paradigm. Now, however, we’re seeing success because we can take a PDF and turn it into something interactive. Some of it comes down to how cleverly you design the PowerPoint or InDesign file.
What’s your take on that? Was it just underdeveloped at the time? Or was it simply too early—was there not enough demand for deep interaction back then?
0:15:02 - Aaron Dun
Yeah, I mean, look, I’m from a generation that had Choose Your Own Adventure books, right? You’d be on page three, make a choice—if you chose A, you’d go to page 52; if you chose B, you’d go to page 22.
But the central challenge of those books, which still applies today, is that you need a content stream to match each of those journeys. And as those journeys branch out, they grow exponentially. Back in the days of physical books—when kids actually read books—you could only have four or five choices because it wasn’t feasible to expand infinitely.
In the digital world, early interactive experiences tried to replicate this by mapping out decision trees: Make a choice here—yes or no? Each path led to a different outcome, creating parallel tracks for every decision. The early vision for personalized web content at scale was that we’d be able to tailor experiences down to a unique persona.
But that requires a massive amount of content, planning, and effort. And it also asks a lot of the person consuming that content. How many choices will they make before deciding, I’m done, I’m out?
In a sales setting—whether digitally, over Zoom, or in person—the entire engagement is structured to guide prospects through those decision gates and, ideally, close the deal.
But in a more passive setting, where someone is simply consuming content on their own, attention spans are much shorter. You might get them to make one choice, but beyond that, it’s a tough sell.
The assumption used to be that if the experience was engaging enough, people would stick with it. We even tested this back in the day: after someone filled out a demo request form, we would push additional content to them under the guise of setting up the context for the demo. And we saw strong engagement—people moved through that experience at a high rate.
But at that point, they had already filled out the form. We had already counted them as a lead and routed them to sales. It’s different when someone is still in a passive setting. Getting them to engage meaningfully is much harder.
Then there’s the question of expectations—what does success actually look like? And ultimately, is the juice worth the squeeze?
If 1,000 people download a PDF, but only 12 engage with the interactive experience, is that a win? It might be an incredible result. But structuring that kind of experience effectively is a real challenge.
A few things we’ve been seeing…
0:17:45 - Alex Shevelenko
I'd love to get your reaction through the lens of being an operational CMO. So, there's this tension where you could lose leads if you gate content, but those leads will be higher quality. In fact, you've spoken about this before—that marketers should stop counting leads and start focusing on high-quality MQLs (Marketing Qualified Leads) that are actually engaged and willing to buy. That’s still true, obviously. However, we've found that this doesn't have to be a strict dichotomy.
If you delay the gating, the drop-off is still huge. For example, if you present the world of free content, and then this somewhat obnoxious marketer asks me to fill in my personal details just to be bombarded by reps before I know what’s in the content, the friction is too high. You’re looking at a 90 to 95% drop-off rate in that scenario. But imagine delaying that gating. You engage with the audience first—more on that later—and at the end, you could have more people exposed to your content. Since you're not gating the content upfront, more people will see it. Then, because more people are exposed, a higher percentage of the right ones will be genuinely committed and will still fill out the form to download something else, for instance. So, you're going to get both more education and more leads. The leads you'll get will be the ones who have actually read your content, so they're already in the sales process. They might even move from “I filled out my information” to the next step: scheduling a meeting.
That’s the real gold star—meeting bookings, not just being reached out to by someone. We've seen this in one particular case. So, does that feel right? Are we breaking that dichotomy of losing leads by delaying gating?
0:19:54 - Aaron Dun
In the purest form of theory, as taught in marketing classes in business school or undergrad, or as espoused by influencers on the internet, you want to build an engaged audience with your ideas. The companies or teams that deliver the best ideas, ideas that resonate most clearly with their intended audience, will win. So, with that overarching statement in mind, if you stipulate that it’s true, your job is to deliver your ideas in a format that is easily accessible and consumable, one that your prospects want to engage with and find themselves in. If you do that, it's amazing. You can make all your content free and bet on the future. They will come to you eventually.
It’s the eventually part that trips up 95% of marketers. Very few companies have figured out how to “catch the tiger by the tail” and can build an engine based on waiting for people to come to them. HubSpot obviously built their entire business this way, but they were really early. There are other companies we're seeing today that are creating momentum—HockeyStack comes to mind. But still, most companies are in this mindset of, “Hey, I need to deliver a number—hopefully revenue, but more often than not, MQLs,” leaving that discussion aside for now, on a monthly basis.
When you’re in that mode, you have to figure out how to balance the desire for your ideas to win in the marketplace (because, eventually, that will bring people to you) with the need to deliver something that the sales team can work with today. The tension between those two is the problem. But delaying the gate is part of the solution, right?
0:22:02 - Alex Shevelenko
Potentially, yes. Because it’s one of the solutions, right? Potentially, yes, because it’s one of the ways to achieve both objectives. We can get the value of both, and that’s what I don’t like—this idea of “it’s one or the other.” I think that’s not creative enough. Sorry, marketing thought leaders. Can we be creative?
The other theme here is the assumption we discussed earlier—that you're going to engage people. That assumption is no longer valid unless they're, you know, really enthusiastic about your content, like they’re eager to buy. That world doesn’t really exist anymore. And even then, their consumption patterns could be very different if you're talking about Gen Z versus, you know, a senior decision-maker who’s been with the organization and needs to give final approval. But they all might want to start easy, start small, and then dive deeper.
My thought process on this is that, when you brought up different mediums, maybe the channels are somewhat similar. I think there’s some blurriness between mediums and channels. For example, let's talk about short-form video. Imagine you had a series of connected TikTok-style videos, but they aren't fragmented. They're connected and a little bit of TikTok, a little bit of substance. Sometimes a video is a great pause, like, “Oh, I don’t have to think too hard here. I can just watch something.” But then, reading something short and punchy reinforces the message and gets us to be more active. But reading 20 pages of wall-to-wall text? Not happening. That wouldn’t work.
So, the idea that a white paper is just a paper? That’s messed up in today’s world. A white paper may be structured like one, but it needs to include active elements that allow me to take mini breaks. Maybe a case study in there doesn’t lead me away from the white paper entirely to watch politics on YouTube, but it keeps me engaged with the experience. I get a little snack, then I’m encouraged to move on and consume something healthier. Healthy content, that is! It needs to have, like, healthy dressing and flavors that encourage me to go deeper. What’s your thought process on this cross-media experience?
0:24:53 - Aaron Dun
Yeah, I think the channel you use, where you're engaging, matters greatly. Who you're engaging with also matters. And, where are they in their buying process? If you’re engaged with a company and trying to decide how to think about ROI, you’re probably going to read a 10-page document on how the product works. Fine, that makes sense, but you're not going to read that at the beginning of the process. Marketers have gotten really good at tailoring content to fit the funnel stage.
However, there’s a tension between where we think you are in the process and where you actually are as a prospect. We’re getting much better at figuring that out. The one channel that’s new in the last five years, which we haven’t talked about yet, is communities of like-minded people. What we’re seeing is that smart companies figured this out before everybody else. Your prospective buyer personas are likely involved in a community of like-minded people that you’re not part of. And, it’s a little bit tangential to what you’re talking about, but the concept is similar. You’re not in that community, and you probably actually can’t get in, because it’s gated. It’s closed to vendors, and they don’t want you in there. They want to share ideas amongst their peers.
Some companies saw this trend and started acquiring communities. For example, Pendo bought a community, HubSpot bought one, and others did the same. ConnectWise bought a community and did a great job managing it. Rapid7 also bought a community, and all those companies did a fantastic job keeping the community intact while also engaging with it. 6sense did an amazing job of building a community of marketers, and we all know that 6sense is running it. But they’re really good at staying out of the discussion while still being a part of it. That’s a really interesting paradigm because they’re involved in the conversation without having to inject themselves. It’s really hard to do, but when you think about it, you can’t show up in those communities with a 10-page PDF.
0:27:11 - Alex Shevelenko
Right, right. You're not delivering any value. You can't be salesy. It has to be about adding value.
0:27:17 - Aaron Dun
Creating that engagement and thinking about where people are, and meeting them where they’re at with what they need, is incredibly hard today. It has been hard forever. But, you know, simply saying, "Hey, I’ve got this content for where you are in the funnel. I think you're at this stage of the funnel. Here’s the content," just doesn’t work. The messages are way more bifurcated than that. The stuff that's happening in that nth-level subreddit you've never heard of, the private community you didn’t even know existed because it's so closed—reaching those moments is tricky.
0:27:52 - Alex Shevelenko
You know, that’s where the power of your own community comes in—how you engage your advocates, your customers, and how you engage your advocates while creating content that makes them want to advocate for you. Content that shows you offer remarkable value, and obviously, something more engaging and interesting than a 20-page PDF. Got it. Amazing.
Aaron, it’s so great to reconnect. It’s tremendous to have you on. How can people follow you, find you, and support you?
0:28:21 - Aaron Dun
I’m on LinkedIn, like we all are. You can find me there at [LinkedIn link] slash Aaron Dun with one "N." I also have a Twitter (excuse me, an X) account, but I don’t really use it much, so follow me on LinkedIn.
0:28:33 - Alex Shevelenko
Awesome, Aaron. Thank you for joining us.
0:28:35 - Aaron Dun
Alex, thank you so much. Great to connect!