See show notes for this episode: S 02 | Ep 13 The Human in the Loop: Why Great Marketing Still Needs One.
0:00:04 – Alex Shevelenko
Okay, okay. Welcome to Experience-focused Leaders. I’m delighted to introduce you to Randy Wootton — a content marketing pioneer, three-time CEO of SaaS companies, and now helping CEOs wrestle with the go-to-market elephant and build massive businesses. Randy, welcome to the pod.
0:00:31 – Randy Wootton
Thanks so much, Alex. I don’t know if I was so much a pioneer as someone just trying to hang on to the tailhook as this whole thing transformed and morphed. It’s been a wonderful journey, so I look forward to chatting about it and sharing some stories and war wounds.
0:00:46 – Alex Shevelenko
Well, look, some of these companies — they’re well-known. A little company named Salesforce, Rocket Fuel (acquired by Sizmek), and then Percolate, which really helped define the content marketing platform category. That got acquired by Seismic, a sales enablement leader, and you’re still continuing to be involved with companies like that. You’re on the board of Opal.
So I want to dig in, because a lot of our audience is interested in the challenges of marketing and sales coming together — and, more broadly, the opportunity to scale the content engine. I think some of it looks very different for our customers who are in regulated industries or functions. They have a lot more constraints. You were helping brand-oriented companies that maybe had some corporate constraints but operated in different markets.
So let’s dig in: what have you seen change from, say, the Percolate days to today — in how the category evolved and how the solution around content marketing has shifted?
0:01:58 – Randy Wootton
Well, if we start with Percolate — I joined after it had been founded. I came in sort of during the last chapter to help it evolve from what it started out as, which was a social media monitoring tool.
And what’s interesting is, I do think that was really the revolution of content — with social media and this idea of: how do you think beyond eBooks, emails, and websites into something dynamic, playing out in near real time?
There were a bunch of companies that kind of sprung up like mushrooms — I think of Buddy Media and a couple of others. Salesforce bought one for a crazy amount. I think they bought Radian6 for a crazy amount of money. Remember, Benioff was like, “Everything’s going to be social.”
0:02:39 – Alex Shevelenko
Benioff is the best at switching to whatever’s the latest flavor of the day — whether we’re ready for it or not. At Salesforce, that’s kind of the point. Whatever the wave is, we’re going to be on top of it — and that’s actually a skill in itself. It was brilliant. Every year.
0:02:57 – Randy Wootton
He came out with Dreamforce, and it was always, “What’s the next cloud?” — Sales Cloud, Service Cloud, Marketing Cloud, Analytics Cloud, Social Cloud. But he’s one of the most brilliant marketers out there, and it was a forcing function for all of us.
I spent a couple of years there, and there was a rhythm — bringing a huge number of people together for launches and to wow the world. He was doing content marketing in a way that no one else was.
Percolate had its origins in this idea of social media management — basically, how do you make all this work?
When I joined the company, we were transitioning to content marketing more broadly across all channels. I used to describe it as: I thought marketing would start to move at the pace and pattern of social.
Meaning — remember when social first came out? Something would pop on Twitter, and you’d have to respond immediately. Then you’d want that message to play out across your other channels — send an email, update your website — to create this real-time interaction with customers that had never happened before.
Before social, brands would put out content and just… let it sit.
0:04:10 – Alex Shevelenko
It would stagnate there for a while. You’d be lucky if it even had the current year in the footer.
0:04:17 – Randy Wootton
Exactly — and there was no feedback from customers, no real-time response. Social enabled that ongoing dialogue. So the question became: how do you manage that conversation?
That was the first big shift. The challenge at the time, for those who remember, was that each marketing distribution channel had its own tech stack. You had an email solution, a website solution, a social solution — and none of them worked together.
One of the things we were trying to do at Percolate was build a content hub — to create orchestration. How could people understand the overarching brief, plan how to build their assets, and then plug into those distribution systems?
So you’d go from systems of orchestration and production to systems of distribution — all coordinated and tied to data. You’d tag every piece of content, then loop back to see what was working. That was really the bridge.
When I talked to Doug Winter, who was CEO of Seismic, they were thinking about sales as a channel. The conflict at the time was: marketing would produce assets that sales wouldn’t use. Sales would say, “Marketing’s assets suck.” Marketing would say, “We’ve given you all these assets — you never use them, so we don’t know how to get better.”
Doug and I thought we could connect those worlds — have content marketing anchored in the CMO’s office, bridge it into sales enablement (a category Seismic was leading), and then have everything tagged so data could flow back to marketing. That way, marketers could improve their content based on what sales actually used.
That was the thesis — and that’s what we did for a couple of years. Then I left, and I don’t know what’s happened since.
0:06:06 – Alex Shevelenko
What’s your gut level take? When I observed the industry, I remember seeing that acquisition and thinking, Wow, that’s interesting. Finally, sales and marketing are going to have a love affair — they’re not going to fight with each other anymore. Nobody’s going to get blamed for bad leads, and marketing won’t complain that their content isn’t being used properly. We all know that story.
I’ve worn both sales and marketing hats in the past, so I can see the potential. But when I look at most sales enablement vendors — not just Seismic — I think they mostly talk to marketers because marketers are influencers and they distribute the content through those systems. But they’re not really marketing platforms. At the end of the day, they’re still very sales-focused.
Content, for the most part — with some exceptions we’ve talked about — is still more sales-oriented. It doesn’t have that marketing flair. Maybe there are a few interactive content pieces squeezed in there, but I think that’s a big missed opportunity. It never really connected.
That’s my thesis — because in today’s world, the best salespeople use AI-scaled marketing techniques to personalize outreach to a much larger number of prospects and create more self-guided buyer experiences. Meanwhile, the best marketers think like sellers — not just delivering leads, but really driving pipeline. They focus on turning lower-end segments into revenue and delivering highly qualified customers to the sales team.
I’m not sure that vision has really clicked yet when I meet some of our customers. It happens — but usually in smaller teams, where the marketing person literally sits next to sales and supports them directly. That’s where you see the alignment. But once you get into larger organizations, I’m not sure the dots connect anymore. What’s your take — and did you manage to make progress there?
0:08:36 – Randy Wootton
There’s a spectrum, right? What I saw at Seismic was that when there was tight alignment between the head of sales and the head of marketing — sometimes both reporting to one CRO — things worked well. When a CRO says, “Look, we’re spending a bunch of money on technology, but the data isn’t connected. We need a consolidated stack,” they’ll often invest in something like go-to-market ops instead of just separate marketing ops and sales ops.
That usually involves sales enablement and sales training — a center of excellence focused on driving efficiency and effectiveness. When that happens, it works.
One of the reasons Seismic was really successful is that, unlike many companies that start SMB → mid-market → enterprise, Seismic started at enterprise. They were able to handle the complexity of large organizations — tons of users, admin layers, and processes. So they could support enormous companies — I can’t name names, but you can check their website. We’re talking about tens of thousands of salespeople and marketing teams across multiple countries trying to coordinate and distribute information.
So I’d say, for big enterprise use cases, if there was alignment, it worked. If not, they fought.
On your second point — yes, a lot of sales enablement tools are still primarily sales enablement tools. Their focus is getting content into sellers’ hands so they can use it with buyers. I agree — sales enablement was never designed to be marketing.
I sit on the board of another company called Opal — we used to compete with them at Percolate. They’ve had great success with some incredible brands, often B2C, because they approach it from a marketing perspective — solving the marketing orchestration problem.
They focus on how a CMO sets up objectives for the year, translates those into quarterly and monthly campaigns, and then executes on that strategy. So while Opal isn’t as tightly integrated with Seismic as it could be, I think Seismic — with the legacy Percolate content marketing orchestration — is further along in offering an integrated solution than some other sales enablement providers that started purely in sales.
0:10:54 – Alex Shevelenko
Right, because of that history — and at least the belief that it was worth investing in. But it’s hard.
0:11:04 – Randy Wootton
Yeah, and the only other point I’d make is about budgets — who pays for it? It always comes down to that. Unless you have a CEO aligned with the go-to-market team, thinking about technology investments across functions, marketing will say, “I’m spending my budget on 6sense for intent data — that’s where I see the most value.”
Sales will say, “I’m spending mine on Gong because I want to improve forecasting.”
But you really need a strong RevOps or Go-to-Market Ops leader who can step back and say, “No, when we think about overall impact versus value, having a system that lets us distribute and measure content effectiveness — that’s worth it.”
And that’s my hope.
0:11:46 – Alex Shevelenko
When the title of CRO started coming up, I thought — finally! Finally, it’s not a Chief Sales Officer; it’s a Chief Revenue Officer. But I think eventually “CRO” just became another word for “Head of Sales.”
I think there are different types of CROs, sure, but if we’re talking about the 80th percentile — I was with you in thinking, finally, they get it. They get that it’s about revenue, that everything should align.
And I think, theoretically, yes — it does happen. But it happens, like you said, when there’s strong leadership or when people have really run into big problems and decide to fix them. You need to sit in the problem long enough to actually change the dynamic.
We were talking earlier — even within marketing itself — it’s great if we can bring marketing and sales together, but they all live in different tools. So we have to start thinking: can we build a tool or a platform that actually works for both? And that’s very hard.
Because, for example, Gong has very different DNA than 6sense, and so on. The tooling itself is fragmented. And as you said, marketing is so bifurcated and technically complex — you’ve got people focused on one tactic, one type of content, versus demand gen folks. They all have their own tools and workflows. It’s hard to even bring marketing together, much less marketing and sales.
So what does that mean?
0:13:25 – Randy Wootton
Yeah, well, I think you see that with the big clouds — like Salesforce, which we talked about earlier, trying to build out a marketing cloud. They basically bought ExactTarget, which was a mass email system, and within that was Pardot, a B2B email platform. (I won’t comment on either.) Then they bought Buddy Media and tried to bring that all together — but the systems never really worked.
What you see with Salesforce — and the same is true for Microsoft and Oracle — is that unless the technology is built from the ground up with a shared foundation, it doesn’t work. You’ve got to go down to the bare metal.
What I mean by that is you need a common architecture — a shared data structure. What do you mean by a lead? By an opportunity? An account? A channel? Content? How is that data tagged and captured? Because now, as we move into AI, you’re putting an intelligence layer on top of all of it.
If you don’t have an architecture to support it, it’s madness. Think about marketing attribution — there are so many systems trying to tell you, “When you spend money on X, how does it compare to Y?” I’ve had so many — not arguments, but heated discussions — with marketing teams over LinkedIn versus G2 versus email, and then sales is operating in a completely different channel.
Should you hire another BDR? Should you invest more in content? It’s so hard to have one source of truth across all of go-to-market because the data structure is distributed, captured at different times, and affected by things like near-real-time or programmatic advertising. It’s just wackadoodle — incredibly complicated.
0:15:00 – Alex Shevelenko
Yeah, and I think when I reflect on our journey building RELAYTO — we found that marketers, even in very complex enterprise setups, who work closely with sales — really roll up their sleeves and support big proposals — those marketers have a much better pulse on connecting the dots.
They tend to be account-based marketers — they know the campaigns, the prospects, the nuances. They use us for top-of-funnel work, sometimes for ABM, but always in a very targeted way. They know how to apply it properly, all the way through to creating a digital buyer experience or proposal that actually closes.
That partnership works well in pockets where there’s no hiding behind tools or reports. The teams are deeply aligned and often colocated — like having a marketer embedded with sales, just like an SDR supports salespeople. When you have those little pods — marketers working closely with the sales team — good things happen.
When you don’t, you might get scale, but you also get a lot of friction along the way. That’s what I’m seeing, at least.
0:16:31 – Randy Wootton
Well, think about this — one of the hardest reasons CMOs have such a short lifespan, about 18 months or less, is because marketing covers such a broad range of capabilities.
On one end, you have database marketers and demand gen folks. On the other, you have brand people — visual identity, voice, tone — and content or thought leadership marketers. In the middle, as you mentioned, is product marketing.
Product marketers need to understand the product deeply enough to engage in sales cycles and add value — to listen to a prospect and say, “I understand the problem or opportunity here. I know the capabilities that can help and can translate that into content.”
That’s a very different skill set from demand gen, which focuses on optimizing search results, or brand, which is about creating a compelling experience.
What happens is that depending on the company context — and the CEO’s orientation — if leadership isn’t clear about what the company really needs from its CMO, they end up hiring the wrong kind.
And I also think there’s a strong argument that positioning, messaging, and category creation are skills unto themselves — very different from traditional brand marketing.
0:17:55 - Alex Shevelenko
It's different from product marketing. So, yes, I think typically it's too important to be left only to marketers. Because marketers might revert to Gartner categories, trying to out-compete iteratively in existing spaces where they can get leads—since the leads are already there. But true category design breaks through that. It shapes the narrative and takes you into areas where marketers generally don’t even have the mandate to go.
0:18:31 - Randy Wootton
Yeah, but the best marketers—what I’d call strategic marketers—are like the right hand of a CEO. When I’ve had great thought partners, we can talk about corporate strategy and where we need to go. That needs to translate into a narrative—a corporate narrative—that then turns into positioning and messaging.
So, to your point: do you have marketers who can do that? I have people I know and bring in as consultants for this. Bob Wright from Firebrick is probably one of the best in the world at it. This is all he does. He also wrote Traction Gap, which I recommend to any CEO.
I’m working with him on a client right now, and just watching his magic—how he thinks about category design and translates that into a marketing blueprint, positioning, and messaging—is incredible. So to your point, Alex, I think that leads everything else. You can’t do marketing unless you’ve nailed your positioning.
And as a CEO, especially if you’re a technical founder and your audience is mostly technical, go find one of these people—or call me, or connect with me—and we can put you in touch. Because nailing that story, that crisp narrative, is everything. It aligns perfectly with what Christopher Lochhead, who wrote Play Bigger, talks about.
0:20:02 - Alex Shevelenko
Yes, Christopher Lochhead. Funny you mention him—we just interviewed him for the pod yesterday, so it’s fresh. And I agree, it’s an entirely different skill set. You still need to understand what marketing needs to do—you still have to deliver the category, launch it effectively, and spread it—but it’s a completely different mindset. So, going back to your point, that’s a very specific skill set.
0:20:30 - Randy Wootton
If you’ve hired a CMO for that, that’s what they’re going to do. They’re probably not going to be as strong in demand gen, but they’ll need to build a team and structure to support it.
And just because you have positioning figured out doesn’t mean you can create compelling social content or email content. So how do you orchestrate content effectively?
I still fundamentally believe—and we might not have said this at the start of the podcast—that content is the atomic unit of communication. Even in an AI-powered world, people process information through content. That’s the capsule everything travels in. And I think people undervalue it.
Look, I was an English major. I taught literature. I believe in the well-written word. I even have a Substack, so I get it.
0:21:18 - Alex Shevelenko
I have a bias too—but you’re someone who came from content, from being an English major, and became a CEO in a very technical, finance-driven space. That’s an important distinction.
0:21:36 - Randy Wootton
Yeah, you’re right. That’s exactly why I’ve always leaned into it. Writing compelling words and influencing people has been the most rewarding part of my career. Content is the vehicle for that.
And we’re on the cusp of another generational shift. Everyone’s talked about it, but content will change dramatically. I’m writing a book right now, working with AI to do it, and my idea of what a ghostwriter, copy editor, or research assistant is—has completely changed compared to three years ago. That shift will change how marketers think about communication for brands.
0:22:19 - Alex Shevelenko
On that note, one of the things we’ve observed is that everything is leaning toward content overwhelm. Some of it will be done well—by people who know how to train the platform and already have years of experience in creating content. But a lot of it will come from outsourced teams without subject matter expertise, just regurgitating what they get from OpenAI.
So, in that world, I want to put myself in the shoes of the consumer and ask: what would a consumer need to see to trust the content?
Because let’s assume everyone will be able to create content—that part’s inevitable. The real question is: what makes someone trust it? What makes them experience it amid the deluge of content they’ll encounter daily? How do they move beyond “oh, another piece of content” and actually engage?
If you catch someone’s attention, how do you turn that trust and experience into a meaningful next step in their journey—especially now that the cost of creating content is basically zero?
0:24:05 - Randy Wootton
Yeah, you know, what I would say is that I think we’re in the awkward teenage years—or maybe even childhood—of this whole evolution. I do think everyone’s going to have their own agent, and that agent will do a lot of filtering and research.
It’s like, you know, I don’t need to buy a new refrigerator until I need to buy a new refrigerator. But when I do need one, I want to find all the right content.
No one’s doing traditional search anymore. G2 is dropping off a cliff, Google search is declining—we’re seeing the death of the blue link. People aren’t using Google search the way they used to for purchases. Even Google itself is putting AI results above the blue links.
I do all my research in ChatGPT now—anything I want to buy.
So, unless you’re a brand that’s optimized for LLMs and can get your brand into that consideration set, you’re completely out. Because the way people are accessing information is changing—just like during the SEO and SEM revolution.
There was a company called SEMrush that helped drive the rise of SEM agencies. Now there’s a guy, Todd Paris, CEO of a company called IQRush, and they’re optimizing brand placement in LLMs. I think that’s the next battleground—especially in B2C.
When I’m using ChatGPT and say, “Hey, I want to buy a new car, I care about speed versus fuel efficiency,” and then add more variables—if I had an agent who already knew me, I wouldn’t have to train the prompts. It could just say, “Here are four cars for you to consider.”
Same thing with something like protein powder. I’ve gone down the rabbit hole lately—what kind should I take at different stages? Instead of doing 50 Google searches, I just do one ChatGPT query and refine it a couple of times.
So, to your point—the way consumers buy is changing radically. The brands that learn how to intercept that shift, understand the evolution of content, and create, distribute, and personalize effectively—those are going to be the winners. Those that don’t will be the losers.
0:26:43 - Alex Shevelenko
Brilliant. Last question. Seismic had a strong presence in regulated content and regulated verticals.
A lot of our customers also come from corporate communications functions and publicly listed companies. They can’t take a chance that, say, their annual report will be written entirely by AI—but they still want someone, whether it’s an analyst or a bot, to consume it effectively.
Likewise, there are niche industries like employee benefits—highly regulated—but every U.S. employer around this time of year has to figure out enrollment. Companies are spending around $24,000 per employee on benefits, and nobody really understands what they’re getting. HR barely understands it, employees barely understand it, and benefit advisors end up answering the same questions over and over again.
So that’s an example of regulated content where you can’t trust a generic LLM to generate answers without risking compliance—or even lawsuits.
What do you think will be the approaches that actually succeed in that kind of environment?
0:27:59 - Randy Wootton
Yeah, well, I think the biggest challenge with LLMs today in terms of content creation is that they operate in a stateless environment. It’s hard to trace the source of information and ensure consistent compliance and governance.
That problem hasn’t been solved. In the past, companies controlled their content and had ways to do quality checks.
So, I think you still need a human in the loop—someone overseeing augmented content generation and doing final QA. You could even have agents acting like paralegals, checking for risks, misuse of brands, or missing trademarks.
But in the meantime, you’ll need checklists, audits, and documentation—tracking sources and verifying compliance. That way, you can produce an output that confirms the content aligns with objectives and is accurate at least once per quarter.
Until then, this messy, stateless environment—where sources and compliance are uncertain—makes it hard to trust LLM-generated content fully.
0:29:12 - Alex Shevelenko
Randy, this was super fun. Where can our audience find you if they want advice on how to scale their business?
0:29:20 - Randy Wootton
Yeah, probably the easiest way is through my advisory service called CEOX. I’ve got a few things I’m working on under CEOX.io.
I’m always available on LinkedIn, and if you want to reach out directly, it’s [email protected].