The Prompt

Mark Drosos, Conductor’s SVP of Channel Sales and Alliances, connects horse training with AI credibility. He explores how consistency builds trust, why AEO must move beyond chasing citations, and how brands can become “agent selectable.” The conversation covers AI as a buying-group member, persona-driven content, verticalized agents, and the race to own consensus.

AI can make people productive before it makes them experienced. That creates a new problem for leaders: if junior employees stop doing the work that once taught judgment, where will the next generation of experts come from?Elizabeth Maxson, CMO of Contentful, joins Rachel Truair to explore what her team calls “judgment debt”—the long-term cost of automating away the experiences people use to build instinct, context and expertise. They discuss why Elizabeth still requires humans to write the brief, why knowing when AI is wrong may become more valuable than knowing how to use it, and why she believes leaders need a “human on the hook,” not simply a human in the loop.The conversation ultimately asks whether businesses can capture AI’s efficiency without accidentally dismantling the apprenticeship system that creates their future leaders.Quotes“You have to build judgment by actually doing the work and having lived experiences.”“I want to shift ‘human in the loop’ to ‘human on the hook,’ because if something does not work, who’s accountable? We are.”“Do you have enough expertise to know when it’s wrong? And if you don’t, do you at least have enough expertise to ask the question to figure it out?”From the conversationWhy automating entry-level work could create a long-term shortage of judgment, skills and institutional knowledge, even if nothing appears broken today.How Elizabeth separates work AI should accelerate, such as analyzing large data sets and creating a “crappy first draft,” from the strategy, curiosity and accountability she believes should remain human.Why Contentful still requires humans to build detailed briefs, and why Elizabeth believes some organizations may need to “go slow to go fast” instead of treating speed as the objective.What “judgment debt” looks like when people rely on AI before they have enough experience to recognize when its answers are wrong, and why mentorship and human relationships still matter.How hiring may change when candidates use AI to produce excellent work: Elizabeth argues leaders should test the thinking, response to feedback and decision-making behind the output rather than simply banning the technology.About the guestElizabeth Maxson is the Chief Marketing Officer of Contentful, a content management platform trusted by more than 4,200 companies around the world.Elizabeth brings nearly two decades of integrated marketing leadership to the role and is focused on driving marketing strategies that leverage AI and personalization to help brands deliver personalized and scalable content to their audiences.Prior to Contentful, Elizabeth served as the Chief Marketing Officer at Tableau, a Salesforce company, where she led go-to-market strategy and drove end-to-end marketing initiatives. In addition to her role at Tableau, Elizabeth has also served as the Head of Marketing at Quip, another Salesforce acquisition, as well as spearheaded Strategic Technology Partnerships marketing, launching critical relationships with industry giants such as AWS, Google Cloud, Alibaba, Apple, and many others.She carries a BAA in Facility Management and Marketing from Central Michigan University.LinkedIn: https://www.linkedin.com/in/emaxson/

The internet used to make a simple promise: create something valuable, get discovered, and earn the visit. That promise is disappearing as Google answers questions on the results page, social platforms suppress outbound links, and AI tools summarize sources without sending them traffic. Rand Fishkin, CEO and cofounder of SparkToro, joins Rachel Truair to ask whether adapting to this zero-click era also helps cement it. Rand explains why attribution rewards the platforms that capture demand rather than the channels that create it, what marketers should measure instead, and why falling traffic may push the industry back toward brand, creativity, and work people genuinely remember.The question underneath it all: when every rational marketing decision sends us deeper into closed platforms, are we surviving a broken internet or helping break it?QuotesThe zero-click playbook"Your job is to go to the places where your audience pays attention."When AI gives you an answer without the source"Check for the source every time. My God, you can't trust those things."Brand building in a zero-click world"Brand building is about being present in people's sort of daily lives and habits."From the conversationHow Google Ads can take credit for demand created by a podcast, PR, content, or an event - and why that distorts the next budget decisionWhy zero-click search has accelerated since 2024 as Google, social networks, and AI tools increasingly answer without sending trafficWhat replaces traffic and attribution: finding where an audience pays attention, creating for that environment, and measuring lift and incrementalityWhy the zero-click era may revive brand building, creative risk, and the kinds of marketing that dashboards struggle to proveWhy websites remain essential even as visits decline, and why Rand now believes "don't build your home on rented land" is outdated adviceAbout the guestRand Fishkin is CEO and cofounder of three companies: SparkToro, makers of fine audience research software, pun-filled Google Alerts alternative Alertmouse, and indie game developer Snackbar Studio.He’s the co-author (with Amanda Natividad) of the upcoming Zero Click Marketing and 2018’s Lost and Founder. When Rand’s not working, he’s usually traveling with or cooking a fancy meal for the love of his life, bestselling author Geraldine DeRuiter.Rand was, in a past life, the CEO/cofounder of Moz, and Inbound.org. He’s keynoted hundreds of events around the world on marketing, technology, and entrepreneurship and his research has been cited by the US DOJ, FTC, Wall Street Journal, Washington Post, Economist, alongside thousands of other publications.LinkedIn: https://www.linkedin.com/in/randfishkin/

We've spent nearly two decades trying to make selling easier, CRMs, automation, sequences, intent data, and now AI. So why does it feel harder than ever to actually earn a buyer's trust? Jen Allen-Knuth, founder of DemandJen, joins Rachel Truair to explore whether sales technology was ever really built for the buyer, or whether it mostly optimized the seller's side of the interaction. Jen makes the case that “personalization” has become one of the emptiest words in sales, breaks down what actually makes a cold email work, and gives her honest read on whether the sales profession shrinks as AI takes over research and outreach. The question underneath it all: if every piece of sales technology disappeared tomorrow, what would still make one human worth talking to?Quotes"I think if we continue on as we have, there is going to be a much smaller number of people that are gonna sit in a sales profession.""Personalization has been one of the worst terms to ever come out of sales or marketing because it's not specific enough to mean anything.""In sales, the hard work works because it's hard. Most people choose easy."From the conversationWhy so much of sales technology has been built to optimize the seller's side of the interaction, not the buyer'sWhy “personalization” has become one of the emptiest words in sales and marketing, and what real relevance looks like insteadWhat separates a cold email that gets a reply from the hundreds that get ignoredWhether the sales profession shrinks as AI takes over research, writing, and outreach, and where a human still earns their seat at the tableWhy customer stories are sales' most underused asset, buried in an LMS while reps lean on self-congratulatory slidesAbout the guestJen is the founder of DemandJen, a sales training and consulting company focused on helping GTM teams break through the status quo and avoid losing pipeline to buyer risk aversion. As a keynote speaker and sales trainer, she specializes in equipping sales teams selling into enterprise and mid-market with the tools to overcome customer hesitation and close more deals. Jen brings in-depth strategies to help teams confront the fear of change and risk, and she's a go-to for sales kickoffs and workshops that drive success.LinkedIn: https://www.linkedin.com/in/demandjen1/

New research on thousands of professionals found something leaders don't want to hear: 53% of individuals say they're already deep into using AI, while only 25% think their own organization has caught up. Mike Kaput joins Rachel Truair to push that gap down one level, past the industry stat, into the team a leader thinks they know. Mike explains why the real barrier is uneven training rather than the tools themselves, makes the case that most knowledge workers aren't ready for the shift from chat to agentic AI, and shares the one question he'd ask any team to find out what's actually happening. The question underneath it all: how sure are you that you already know what your team would say?Quotes“It's less about the tool and a lot more about your approach.”"53% of people said they're already in the advanced stages of using AI. Only 25% said the same about their own organization.""Your average knowledge worker is pretty unprepared for the switch from chat to agentic AI."From the conversationWhy 53% of individuals say they're already in advanced stages of AI adoption, while only 25% think their organization isWhy the gap comes down to uneven training and access, not a lack of desire to use AIWhat's actually different about agentic AI tools, and why most knowledge workers aren't ready for that shiftWhether the future favors specialized, vertical AI tools or the big frontier models everyone already hasThe one question Mike recommends every leader ask their team to find out the truth about how they're using AIAbout the guestMike Kaput is the Chief Content Officer at SmarterX and a leading voice on the application of AI in marketing and business. He is also the co-author of Marketing Artificial Intelligence and co-host of The Artificial Intelligence Show podcast.LinkedIn: https://www.linkedin.com/in/mikekaput/

About the episodeWe're communicating more than ever, and AI has made producing polished language almost effortless. So why does it feel harder than ever to actually move people? Kelly Urban, CMO at Maui Jim and formerly VP of Global Media Relations, Influencer Marketing, and Social Media at GoPro, joins Rachel Truair to explore what's actually changed in how we communicate, and why confidence, not polish, might be the real foundation of persuasion. Kelly makes the case for going to AI last instead of first, explains why trust is harder to earn than attention even though attention gets all the anxiety, and names the one piece of leadership advice she'd erase completely. The question underneath it all: if AI can write almost anything, what's the one thing only you can say with heart?Quotes“Attention can be captured very quickly, but it can go away so fast.”“I think the inflection point is are you going to AI first or are you going to AI last?”“If you can find that magic spot of being very personally connected to your team, you will be able to lead in a way that others can't.”From the conversationWhy getting distribution used to be the hard part, and getting attention is nowWhether steadiness or reinvention actually builds a stronger brandGoing to AI first vs. going to AI last, and why it might decide whether you keep the ability to think for yourselfWhat most leadership advice gets wrong about staying professionally distant from your teamWhich is harder to earn right now, trust or attention, and why that's the wrong question to answer too quicklyAbout the guestKelly Urban joined Kering Eyewear in September 2025 as the CMO of Maui Jim after serving 11+ years as a VP of Marketing at GoPro.  Urban is responsible for driving global brand strategy and expanding awareness for Maui Jim’s sun and optical collections across B2B and B2C audiences internationally. Urban is based out of Kering's Manhattan office.LinkedIn: https://www.linkedin.com/in/kellybaker1/

Generative AI is not just another tool, it’s a complete shift in how decisions are made and work gets done.In this episode of the OnBase podcast, Paul Gibson sits down with Jim Sterne, author and AI thought leader, to explore how organizations must rethink leadership, culture, and ROI in the age of generative AI. They discuss why AI moves us from deterministic systems to creative ones, why traditional ROI models fail, how leadership misalignment slows adoption, and what it really takes to embed AI into workflows without losing human judgment. If you’re navigating AI transformation in your organization, this episode will fundamentally change how you think about it.About the GuestJim Sterne focuses his forty-five years in sales and marketing on using technology for marketing. He sold business computers to companies that had never owned one in the 1980s, consulted and keynoted about online marketing in the 1990s, founded a conference and a professional association around digital analytics in the 2000’s, and has lately been advising companies on the adoption of generative AI. He has written thirteen books on Internet advertising, marketing and customer service including the humorous Devil's Data Dictionary. His first book on AI was “Artificial Intelligence for Marketing: Practical Applications” (2017) and his latest is “The New Science of Customer Relationships: Delivering on the One-to-One Promise with AI” (2025).Sterne has consulted to some of the world's largest companies; lectured at MIT, Stanford, USC, Harvard, and Oxford. Since 2002, Sterne has remained active producing the Marketing Analytics Summit and spent 20 years with the Digital Analytics Association as cofounder and Board Chair Emeritus. He was named one of the 50 most influential people in digital marketing by one of the UK's premier interactive marketing magazines and was included in a list of the Top 25 Hot Speakers by the National Speakers Association. Sterne is on the Advisory Board of a variety of startups, has served on the Boards of his local library foundation and the Better Business Bureau, and the Editorial Board of the Applied Marketing Analytics peer-reviewed journal. His current passion is leveraging generative AI as a catalyst for innovation as seen in his TEDx talk.Connect with Jim.

ABM isn’t a campaign. It’s a behavioral listening system.In this episode of the OnBase Podcast, Chris Moody sits down with Radoj Glisik, SVP of Digital Strategy & Design at Altudo, to explore how account-based marketing evolves when you combine behavioral psychology, customer experience design, and modern data infrastructure.They unpack evaluation patterns, buying group detection, why intent data alone fails, how to structure a marketing data lake, and why ungating content improves outcomes. You’ll also learn how GA4, DXPs, and personalization engines work together to create meaningful account-level engagement.If you’re serious about scaling ABM beyond campaigns and building a system that sales actually trusts, this conversation is essential.About the GuestRadoj Glisik is a battle-tested CX, branding, marketing, and content strategy executive. He has delivered significant results in market research, new market entry, digital product strategy, information architecture, advertising, operational and process design, customer experience, and user testing. Radoj specializes in advanced personalization using behavioural psychology and the JTBD framework.Connect with Radoj.

AI is everywhere in B2B marketing. But most teams are still working with disconnected tools and fragmented data.In this episode of the OnBase podcast, Chris Moody sits down with Dan Rosenberg, co-founder of Octane11, to explore why composable B2B marketing is the foundation for real AI-driven growth. They unpack the myth that ABM is dead, why monolithic marketing clouds fall short, and how connected account-level data allows AI to replace outdated attribution models.Dan shares practical insights on building modular stacks, orchestrating buying groups, scaling multi-channel campaigns, and letting AI interpret what is actually driving pipeline and revenue.If you want to move beyond dashboards and truly connect marketing to outcomes, this episode is for you.About the GuestDan Rosenberg is a thought leader and frequent speaker on B2B data, marketing analytics, and the evolution of modern martech. He’s the Founder and CEO of Octane11, an AI-powered, multi-channel analytics platform built for agencies and enterprise B2B marketers. Previously, Dan served as Chief Strategy Officer and CMO at MediaMath and has held senior operating and investing roles across adtech, martech, private equity, and venture capital. He’s a graduate of Harvard College and Harvard Business School and lives in New York City.Connect with Dan.

AI won’t fix your go-to-market if your operating system is broken.In this episode of the OnBase Podcast, Chris Moody sits down with Yas Dalkilic, head of AI at RAB2B, to explore why adding AI to legacy workflows rarely drives meaningful results. Instead of chasing tools, Yas rebuilt her agency’s foundation, redesigning people, process, platform, and proof to create a truly AI-fluent organization.They discuss why AI belongs in the handoffs, how to build a shared “common brain” across teams, how buying group intelligence changes with behavioral signals, and why human judgment matters more in an AI-driven world.If you’re ready to move from AI curiosity to AI transformation, this episode is your roadmap.About the GuestYasemin Dalkilic is the Head of AI at RAB2B, where she helps the agency and its clients turn complex marketing challenges into practical, measurable systems. With a background in mathematics and programming, she cuts through AI hype to focus on clarity, execution, and what works now, prototyping, testing, and iterating until workflows drive faster decisions and real outcomes. Her guiding belief is that progress beats demos and process beats theater.Before her work in AI and technology, Yasemin was a world-record-holding freediver. Training to dive hundreds of feet in a single breath taught her how to stay calm under extreme pressure and approach the most complex problems with discipline and intent, a mindset she brings to leading AI transformation today.Connect with Yasemin.