The Prompt

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595

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Oct 2026

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About the show

The Prompt is a podcast about the questions shaping the future before anyone agrees on the answers. Hosted by Rachel Truair, the show brings together operators, creators, analysts, academics, and unconventional thinkers for candid conversations that start with a simple prompt and spiral from there. Before the playbooks exist and consensus forms, The Prompt explores the ideas, tensions, and hot takes shaping what comes next in AI, work, brands, business, and human relevance.

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October 29, 202638 min

> Are founders becoming the last trusted institution? — Sydney Sloan

A founder’s story is often a company’s first brand. It is easier to build, easier to believe and easier to trust than anything the company says about itself. Sydney Sloan joins Rachel Truair to ask what that means for the company, and for the founder, when the two become hard to tell apart. She explains why a company brand takes longer to earn trust than a personal one, why the pressure on founders has changed as expectations for growth speed up, and why a logo can feel less like a design choice than a piece of someone’s identity. They also get into how founders and the people around them work together: what good founders see that others miss, why co-founders and leadership teams matter, how to give a new idea a fair hearing without letting it derail the plan, and what a marketing leader should ask a founder before taking the job. The conversation ultimately asks who a company is really built around, and what happens to trust when the answer is one person. Quotes “It’s almost like renaming a child.” (on why a founder resists a rebrand) “For startup founders, their brand is almost more important than the company brand in the beginning.” “I think it’s just harder to build a trusting brand for the company than it is a personal brand.” From the conversation Why Sydney believes a founder’s personal brand can matter more than the company’s in the early days, how a founder story tied to the company’s purpose builds trust, and why that trust is earned in the founder’s own voice on social channels. Why a company brand is harder to build than a personal one, and what erodes trust along the way: inconsistency, too little investment in brand and turnover in marketing leadership. She points to Gong and Snowflake as brands that stayed consistent. How the pressure on founders has changed, from building a $100 million company in ten years to being expected to do it in two, and why Sydney starts with empathy but still argues founders should give their people psychological safety and a clear way of working. Why the people starting companies are getting younger, what experience adds that speed and ambition don’t, and why choosing investors and board members becomes a personal decision for a founder. What good founders see that others can’t: staying close to the problem and the customer, often as the company’s top salesperson, and why the best of them surround themselves with co-founders and leaders who balance their strengths. How Sydney helps a leadership team handle a founder’s next big idea: document the options, size them, choose together and write down what the company is choosing not to do. Her rule of thumb is three priorities, because more than that makes it harder to hit any of them, and the CEO still has the final call. What Sydney would tell a marketing leader working for a founder: ask how they think about marketing before taking the job, bring the customer’s voice into creative decisions, and take the founder along on any rebrand, because for many founders the brand is personal. About the guest Sydney Sloan is a four-time CMO, board member, and advisor who has led marketing at Salesloft, Drata, G2, and Alfresco.. Before that, she spent 17 years at Adobe across its enterprise and developer product lines. Today she's co-founder of the B2B CMO Project with Jon Miller, CMO Advisor at G2, Executive-in-Residence at Scale Venture Partners, and an LP at Stage 2 Capital, advising over 50 B2B founders and marketing leaders on go-to-market strategy, brand and demand, and building for the AI era. Connect with Sydney . Resources: The Growth Framework Model

October 8, 202635 min

> Is earning AI's trust just horse training with better software? — Mark Drosos, Conductor

Horses don’t trust you because you tell them to. They learn from consistency, predictability and what you do over time. Mark Drosos, SVP of Channel Sales & Alliances at Conductor, joins Rachel Truair to explore why that idea has surprising implications for how brands show up in AI. As answer engines increasingly interpret, recommend and eventually select brands, simply creating more content or chasing citations will not be enough. They discuss why the best brand may still lose if AI does not see the right signals at the right moment, how “agent selectability” changes the role of content across the buying journey, and why brands may need to start thinking of AI agents as another audience, or even another member of the buying group. The conversation ultimately asks what happens when brands are no longer trying to earn credibility only from people, but from the machines increasingly helping people decide what to believe, what to buy and eventually what to do. Quotes “I want to own the consensus, not the source.” “Today, it only knows what you tell it to know. And not every consumer knows what to tell it.” “This selectability and this area of being mentioned and cited won’t be enough. You’re gonna have to be authentic about what you do eventually.” What we cover ● Why Mark sees an unexpected parallel between earning a horse’s trust and earning credibility with AI: both depend on consistency, predictability and repeated signals over time. ● Why AEO may follow the same evolution social media did, moving from trying to game a new channel toward genuinely earning the right to participate in the conversation. ● How Mark compares AI discovery to a horse-show flat class, where even the best horse can lose if the judge does not see it at the right moment, and why brands need the right message for different personas, topics and stages of the buying journey. ● What Mark means by “agent selectability,” and why the next challenge is not simply getting cited by AI but helping an agent understand the customer well enough to choose the right product for that person. ● Why AI recommendations still lack some of the verification signals consumers have learned to expect from reviews, influencers and other sources of third-party credibility, and why Mark believes authenticity will become increasingly important. ● Why Mark thinks companies should start treating the AI agent as a distinct audience, rethink how their content maps to personas and buying journeys, and prepare for a future where people increasingly ask and get rather than search and click. About Mark Drosos Mark established himself as a pioneer in human-generated data partnerships well before AI and Big Data dominated industry discussions. He currently leads global partnerships at Conductor, a leader in AI Search and Content Creation. He launched Lodestone, a platform leveraging AI and data to enhance fan engagement for sports franchises and media organizations. While at Bazaarvoice, he led the creation of syndicating premium user-generated content, powering Agentic Shopping Engines with authentic images, videos, and consumer reviews. Prior to Bazaarvoice, at Khoros, he managed the shift toward early chatbots and agents by overseeing the partnership and acquisition of Flow.ai. When Mark is not focused on AI partner ecosystems, his weekends are dedicated to being a horse show dad to his daughter and serving as the versatile "extra guy" for his wife's equestrian enterprise. From hauling horses to repairing well pumps, fences, trailers, and tractors, his hands-on approach to the “dirty jobs” at the barn has led his friends to jokingly call him the Mike Rowe of AI. LinkedIn: https://www.linkedin.com/in/markdrosos/

September 24, 202627 min

> If AI does the entry-level work, who becomes the next expert? — Elizabeth Maxson, Contentful

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 conversation Why 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 guest Elizabeth 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/

September 3, 202635 min

> Are we adapting to a broken internet or helping break it? — Rand Fishkin

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? Quotes The 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 conversation How Google Ads can take credit for demand created by a podcast, PR, content, or an event - and why that distorts the next budget decision Why zero-click search has accelerated since 2024 as Google, social networks, and AI tools increasingly answer without sending traffic What replaces traffic and attribution: finding where an audience pays attention, creating for that environment, and measuring lift and incrementality Why the zero-click era may revive brand building, creative risk, and the kinds of marketing that dashboards struggle to prove Why websites remain essential even as visits decline, and why Rand now believes "don't build your home on rented land" is outdated advice About the guest Rand 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/

August 20, 202627 min

> Did we make selling easier, and buying worse? — Jen Allen-Knuth

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 conversation Why so much of sales technology has been built to optimize the seller's side of the interaction, not the buyer's Why “personalization” has become one of the emptiest words in sales and marketing, and what real relevance looks like instead What separates a cold email that gets a reply from the hundreds that get ignored Whether the sales profession shrinks as AI takes over research, writing, and outreach, and where a human still earns their seat at the table Why customer stories are sales' most underused asset, buried in an LMS while reps lean on self-congratulatory slides About the guest Jen 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/

August 6, 202632 min

> Is your team using AI you don't know about? — Mike Kaput

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 conversation Why 53% of individuals say they're already in advanced stages of AI adoption, while only 25% think their organization is Why the gap comes down to uneven training and access, not a lack of desire to use AI What's actually different about agentic AI tools, and why most knowledge workers aren't ready for that shift Whether the future favors specialized, vertical AI tools or the big frontier models everyone already has The one question Mike recommends every leader ask their team to find out the truth about how they're using AI About the guest Mike 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/

August 6, 2026Episode 126 min

> Is persuasion becoming a lost art? — Kelly Urban

About the episode We'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 conversation Why getting distribution used to be the hard part, and getting attention is now Whether steadiness or reinvention actually builds a stronger brand Going to AI first vs. going to AI last, and why it might decide whether you keep the ability to think for yourself What most leadership advice gets wrong about staying professionally distant from your team Which is harder to earn right now, trust or attention, and why that's the wrong question to answer too quickly About the guest Kelly 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/

March 20, 202635 min

Ep. 589 | Leading through the AI shift: Why generative AI demands new thinking, not just new tools

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 Guest Jim 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 .

March 6, 202632 min

Ep. 588 | Behavioral ABM: Detecting Buying Groups Before the RFP

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 Guest Radoj 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 .

February 26, 202630 min

Ep. 587 | Beyond monolithic martech: how composable B2B marketing unlocks real AI impact

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 Guest Dan 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 .