S 02 | Ep 13 The Human in the Loop: Why Great Marketing Still Needs One

Randy Wootton led revenue acceleration at Microsoft and Salesforce, steered RocketFuel and Percolate through successful exits as CEO, and helped shape Seismic’s strategy through multiple acquisitions exceeding $300M in value. Most recently, as CEO of Maxio (a company formed through the integration of SaaSOptics and Chargify under Battery Ventures) he built a leading financial operations platform serving 2,200+ B2B SaaS customers. Today, Randy leads CEOx, his advisory firm helping AI-first and Agentic AI companies build scalable go-to-market engines and organizational infrastructure.

Key Takeaways

(0:00 - 4:10) From Social Media Chaos to Content Revolution

(4:10 - 8:36) Content Orchestration and the Sales-Marketing Divide

(8:36 - 13:25) When Sales and Marketing Alignment Actually Works

(13:25 - 16:31) The Complexity of Marketing Tech Stacks

(16:31 - 20:30) Why CMOs Last 18 Months (And What To Do About It)

(20:30 - 24:05) Content as the Atomic Unit of Communication

(24:05 - 27:59) The Agent-Powered Future of Content Consumption

(27:59 - 29:20) Keeping Humans in the Loop for Regulated Content

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1. From Social Media Chaos to Content Revolution

Alex introduces Randy Wootton as a content marketing pioneer and three-time CEO of SaaS companies who now helps CEOs address go-to-market challenges. Randy modestly describes himself as someone trying to hang onto the tailhook as the industry changed, though his resume tells a different story. His career spans leadership positions at Salesforce, Rocket Fuel (acquired by Sizmek), and Percolate, where he played a critical role in defining the content marketing platform category before its acquisition by Seismic. This journey positions Randy uniquely to discuss how content marketing has evolved and where it's heading next.

Randy joined Percolate after its founding, during what he calls the last chapter, helping it evolve from its origins as a social media monitoring tool. The company's transformation paralleled a broader industry revolution sparked by social media's emergence. Social media fundamentally changed content dynamics by introducing the concept of near-real-time interaction and distribution beyond traditional channels like eBooks, emails, and websites. Companies like Buddy Media sprang up rapidly to capitalize on this shift. Salesforce, under Marc Benioff's leadership, made aggressive acquisitions like Radian6, driven by the belief that everything would become social. Alex notes that Benioff excels at identifying and riding whatever wave emerges, whether the organization is fully ready or not—a skill in itself.

Randy reflects on his time at Salesforce and the predictable rhythm Benioff established around Dreamforce. Every year brought a new "cloud"—Sales Cloud, Service Cloud, Marketing Cloud, Analytics Cloud, Social Cloud. This forcing function created urgency across the industry. Benioff's approach to content marketing set a standard that few could match, bringing massive audiences together for launches that wowed the world. Randy experienced this rhythm firsthand during his years at Salesforce, where the cadence of innovation and launch became part of the organizational DNA.

Percolate initially focused on social media management but transitioned to content marketing more broadly across all channels under Randy's leadership. He describes his vision for marketing to move at the pace and pattern of social media. When social first emerged, something would appear on Twitter requiring immediate response, and brands needed to coordinate that message across all channels—email, website updates, real-time customer interaction. This represented a fundamental shift from the pre-social era when brands published content and let it stagnate, sometimes not even updating the year in the footer. Social media enabled ongoing dialogue with customers, creating new challenges around managing those conversations at scale.

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. (Randy Wootton)

2. Content Orchestration and the Sales-Marketing Divide

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. (Randy Wootton)

3. When Sales and Marketing Alignment Actually Works

Randy acknowledges a spectrum of outcomes and explains that at Seismic, alignment worked when there was tight coordination between heads of sales and marketing, particularly when both reported to one Chief Revenue Officer. When a CRO recognizes that technology spending isn't delivering connected data and demands a consolidated stack, organizations often invest in go-to-market operations instead of maintaining separate marketing ops and sales ops functions. This unified approach typically includes sales enablement and sales training as a center of excellence focused on driving efficiency and effectiveness across the revenue organization. In these scenarios, the integration succeeded.

One reason for Seismic's success was its enterprise-first approach, contrasting with typical company trajectories that move from SMB to mid-market to enterprise. Seismic started at the enterprise level and could handle enormous complexity—large user bases, administrative layers, and intricate processes. This capability allowed them to support massive organizations with tens of thousands of salespeople and marketers across multiple countries trying to coordinate information distribution. For big enterprise use cases with strong alignment, the solution worked. Without that alignment, teams continued fighting the same battles they always had.

Randy agrees that most sales enablement tools remain primarily sales enablement tools focused on getting content into sellers' hands for use with buyers. These platforms were never designed to be marketing orchestration systems. He points to Opal, a company where he serves on the board and which competed with Percolate, as taking a different approach. Opal has succeeded with major brands, often B2C companies, by addressing the problem from a marketing perspective—solving marketing orchestration challenges. They focus on how CMOs set annual objectives, translate them into quarterly and monthly campaigns, and execute on strategy. While Opal isn't as tightly integrated with sales systems as it could be, Randy believes Seismic, with its Percolate legacy, offers a more integrated solution than pure sales enablement providers.

The budget question ultimately determines technology adoption. Unless a CEO aligns with the go-to-market team and thinks about technology investments across functions, marketing will prioritize 6sense for intent data while sales invests in Gong for forecasting improvement. Organizations need a strong RevOps or Go-to-Market Ops leader who can step back and consider overall impact versus value, recognizing that systems enabling content distribution and measurement effectiveness justify investment. Alex notes that when the CRO title emerged, he hoped it signaled a shift from Chief Sales Officer to true Chief Revenue Officer. However, he observes that CRO often became just another term for Head of Sales. While different types of CROs exist, the 80th percentile still skews toward sales leadership rather than true revenue leadership integrating all functions.

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. (Randy Wootton)

4. The Complexity of Marketing Tech Stacks

Alex and Randy discuss the challenge of bringing marketing and sales together when they operate in different tools. The question becomes: can anyone build a platform that actually works for both? This proves extremely difficult because tools like Gong and 6sense have fundamentally different DNA. Marketing itself is fragmented and technically complex, with people focused on specific tactics and content types operating separately from demand generation teams. Each group has its own tools and workflows. If it's hard to bring marketing together internally, bringing marketing and sales together becomes exponentially more challenging. This fragmentation raises fundamental questions about whether unified platforms are even possible.

Randy points to the big cloud providers—Salesforce, Microsoft, Oracle—as examples of the challenge. Salesforce built its marketing cloud primarily through acquisitions, buying ExactTarget (a mass email system that included Pardot for B2B) and Buddy Media for social, then attempting integration. The systems never truly worked together because they weren't built from the ground up with a shared foundation. Unless technology starts from bare metal with common architecture and shared data structures, integration fails. Organizations must agree on fundamental definitions: What constitutes a lead? An opportunity? An account? A channel? Content? How is data tagged and captured? These foundational questions become critical as companies layer AI intelligence on top of existing systems. Without proper architecture, the result is chaos.

Marketing attribution exemplifies this complexity. Numerous systems attempt to answer: "When you spend money on X, how does it compare to Y?" Randy describes intense discussions with marketing teams comparing LinkedIn versus G2 versus email while sales operates in completely different channels. Should organizations hire another BDR or invest more in content? Without one source of truth across go-to-market functions, these decisions become nearly impossible. The challenge stems from distributed data structures captured at different times and affected by variables like near-real-time or programmatic advertising. Randy describes the situation as "wackadoodle"—incredibly complicated with no clear resolution in sight.

Alex reflects on RELAYTO's journey and notes that marketers who work closely with sales—particularly those supporting big proposals—have a much better pulse on connecting these dots. Account-based marketers who know campaigns, prospects, and nuances intimately tend to use tools effectively from top-of-funnel work through ABM to creating digital buyer experiences and proposals that close deals. This partnership works in pockets where there's no hiding behind tools or reports. Teams that are deeply aligned and often colocated—like having a marketer embedded with sales, similar to how SDRs support salespeople—create successful pods. When marketers work closely with sales teams, good things happen. Without that proximity and alignment, organizations might achieve scale but generate significant friction along the way.

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. (Randy Wootton)

5. Why CMOs Last 18 Months (And What To Do About It)

Randy addresses why CMOs have notoriously short tenures, typically 18 months or less. Marketing encompasses an extraordinarily broad range of capabilities creating unrealistic expectations for any single leader. On one end of the spectrum are database marketers and demand generation specialists focused on metrics and funnel optimization. On the opposite end are brand professionals who think about visual identity, voice, tone, and brand experience. In the middle sits product marketing, which requires yet another distinct skill set. Product marketers must understand products deeply enough to add value in sales cycles, listening to prospects and translating needs into capabilities. This skill differs fundamentally from both demand generation optimization and brand creation.

The challenge emerges when companies aren't clear about what they actually need from their CMO given their specific context and the CEO's orientation. Without clarity about organizational requirements, companies hire the wrong type of marketer for their situation. A brand-focused CMO will struggle in an organization needing demand generation excellence, while a performance marketer may fail where brand building is critical. Randy argues that positioning, messaging, and category creation represent skills unto themselves, distinct from traditional brand marketing. These strategic capabilities require different thinking patterns and experience bases than typical marketing functions.

Alex notes that category design is often too important to be left only to marketers. Marketers might default to Gartner categories, trying to compete iteratively in existing spaces where leads already exist. True category design breaks through those constraints, shapes narratives, and ventures into territory where marketers generally lack the mandate to operate. This strategic work requires CEO-level involvement and thinking that transcends traditional marketing boundaries. Randy agrees, noting that the best marketers—what he calls strategic marketers—function as the right hand of the CEO. When he's had great thought partners, they can discuss corporate strategy and future direction together.

This strategic partnership needs to translate into a corporate narrative that becomes positioning and messaging. Randy asks whether organizations have marketers capable of this level of strategic thinking. He often brings in consultants for this work, particularly Bob Wright from Firebrick, who Randy considers one of the world's best at category design. Wright also wrote Traction Gap, which Randy recommends to any CEO. Randy currently works with Wright on a client project, observing the magic of how Wright thinks about category design and translates it into marketing blueprints, positioning, and messaging. This work must come first—marketing cannot succeed without nailed positioning. Randy advises CEOs, especially technical founders whose audiences are primarily technical, to find these specialists or reach out for connections. Nailing the story and crisp narrative aligns with what Christopher Lochhead discusses in Play Bigger.

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. (Randy Wootton)

6. Content as the Atomic Unit of Communication

Randy emphasizes that just because positioning is figured out doesn't mean organizations can automatically create compelling social or email content. The question becomes how to orchestrate content effectively across channels. Randy states his fundamental belief that content is the atomic unit of communication—even in an AI-powered world, people process information through content. Content serves as the capsule in which everything travels. He believes people undervalue this reality despite its foundational importance. Randy acknowledges his bias as an English major who taught literature and maintains a Substack. His belief in the well-written word runs deep and shapes his perspective on communication and business.

Alex notes the important distinction that Randy came from content and English literature but became a CEO in a very technical, finance-driven space. This unusual background trajectory matters because it brings humanities thinking into technology leadership. Randy agrees, explaining that this background is exactly why he's always leaned into content. Writing compelling words and influencing people through language has been the most rewarding part of his career, with content serving as the vehicle for that influence. The world stands on the cusp of another generational shift in how content functions and gets created. Everyone talks about it, but content will change dramatically in ways we're just beginning to understand.

Randy shares that he's currently writing a book while working with AI, which has completely changed his concept of ghostwriters, copy editors, and research assistants compared to just three years ago. This shift will fundamentally alter how marketers think about communication for brands. The tools and processes for content creation are being reimagined in real time, and organizations that understand this evolution will gain advantages over those that don't. The question isn't whether AI will change content creation—that's inevitable—but rather how brands will adapt their approaches to maintain quality and authenticity while using these new tools.

Alex raises a critical concern about content overwhelm. Some content will be produced well by people who know how to train platforms and bring years of experience to content creation. However, much content will come from outsourced teams without subject matter expertise, simply regurgitating what they get from OpenAI or similar tools. In this environment, Alex wants to understand what consumers will need to see to trust content. Assuming everyone can create content easily, what makes someone trust it? What makes them experience it meaningfully amid the deluge they encounter daily? How do people move beyond "oh, another piece of content" to actual engagement? If you do catch attention, how do you convert that trust and experience into a meaningful next step in their journey—especially now that content creation costs approach zero?

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. (Randy Wootton)

7. The Agent-Powered Future of Content Consumption

Randy believes we're in the awkward teenage years—or perhaps childhood—of this evolution. He predicts everyone will have their own agent that will handle filtering and research. The refrigerator example illustrates this: people don't need to buy a new refrigerator until they need one, but when that moment arrives, they want to find all the right content quickly. Traditional search is dying. G2 traffic is dropping dramatically, Google search is declining—the blue link is dying. People no longer use Google search the way they used to for purchases. Even Google itself now places AI results above traditional blue links, acknowledging this shift in user behavior.

Randy does all his purchase research in ChatGPT now, whether buying cars or researching protein powder types for different life stages. Instead of conducting 50 Google searches, he runs one ChatGPT query and refines it a couple of times. This efficiency represents a fundamental change in buying behavior. Unless brands optimize for LLMs and can place themselves in AI-generated consideration sets, they're completely excluded from purchase decisions. The way people access information is changing as dramatically as during the SEO and SEM revolution. There's a company called SEMrush that helped drive the rise of SEM agencies during that transition. Now Todd Paris, CEO of IQRush, optimizes brand placement in LLMs. Randy believes this is the next battleground, particularly in B2C markets.

The vision extends beyond simple queries. When someone uses ChatGPT to say "I want to buy a new car, I care about speed versus fuel efficiency" and adds more variables, an agent that already knows their preferences wouldn't require training through prompts. It could automatically say "Here are four cars for you to consider" based on stored preferences and history. The same applies to complex product decisions like protein powder, where Randy has explored what types to take at different life stages. The agent model eliminates repetitive research and provides personalized recommendations based on accumulated knowledge about the user. This represents a fundamental shift from search to recommendation-driven discovery.

Randy emphasizes that consumer buying behavior is changing radically. Brands that learn how to intercept this shift, understand the evolution of content, and create, distribute, and personalize effectively will be winners. Those that don't adapt will become losers. The stakes are high because the transition is happening rapidly. Organizations that wait to address LLM optimization risk finding themselves completely excluded from consideration sets that drive purchase decisions. This isn't a future concern—it's happening now, requiring immediate strategic response from brands that want to remain relevant in agent-powered buying environments.

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. (Randy Wootton)

8. Keeping Humans in the Loop for Regulated Content

Alex raises a final question about regulated content, noting that Seismic had strong presence in regulated verticals. Many RELAYTO customers come from corporate communications functions and publicly listed companies that cannot risk having annual reports written entirely by AI, even though they want analysts and stakeholders to consume them effectively. Similarly, niche industries like employee benefits operate under heavy regulation. Every U.S. employer faces annual enrollment challenges, spending approximately $24,000 per employee on benefits that nobody really understands—not HR, not employees, not even benefit advisors who answer repetitive questions. This represents regulated content where generic LLM-generated answers risk compliance violations or lawsuits. Alex asks what approaches will succeed in such environments.

Randy identifies the biggest challenge with LLMs for content creation: they operate in stateless environments where tracing information sources and ensuring consistent compliance and governance remains difficult. This problem hasn't been solved. Previously, companies controlled their content and had established quality check processes. The loss of that control creates significant risk in regulated environments. Randy believes organizations still need humans in the loop—someone overseeing augmented content generation and conducting final quality assurance. Organizations could deploy agents acting like paralegals to check for risks, brand misuse, or missing trademarks. However, this represents an intermediate solution rather than a complete answer.

In the meantime, organizations need checklists, audits, and documentation tracking sources and verifying compliance. This approach allows production of outputs that confirm content aligns with objectives and maintains accuracy, validated at least quarterly. The messy, stateless environment where sources and compliance are uncertain makes fully trusting LLM-generated content impossible without these safeguards. Organizations operating in regulated spaces must build extra verification layers that may slow down content production but protect against serious legal and compliance risks. The cost of getting it wrong in regulated industries far exceeds the efficiency gains from pure automation.

Randy's advice reflects practical reality rather than idealized AI-powered futures. While AI will increasingly augment content creation, regulated industries will need longer transition periods and more robust verification systems than consumer-facing businesses. The technology needs to mature significantly before regulated content can rely heavily on AI generation without extensive human oversight. Organizations that recognize these limitations and build appropriate guardrails will navigate the transition successfully, while those that move too fast toward full automation risk serious consequences.

Alex concludes by asking where audiences can find Randy if they want advice on scaling their businesses. Randy points to his advisory service, CEOX, accessible at CEOX.io, where he works on several initiatives. He remains active on LinkedIn and can be reached directly at [email protected]. This accessibility reflects Randy's approach to sharing knowledge and helping CEOs navigate the complex challenges of building and scaling businesses in an rapidly changing technology and go-to-market environment.

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. (Randy Wootton)

Check the episode's Transcript (AI-generated) HERE.