Best Story Wins

Column Five
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Oct 16, 2025 • 25min

The Missing Ingredient to your B2B Strategy with Jess Ellis from Attentive

When everyone’s chasing quick wins, it’s easy to forget the one lever that compounds everything: brand clarity. But cramming “agentic AI” into your homepage won’t save you, it just makes you sound like the chorus.In this episode, we sit down with Jess Ellis, Head of Brand, Content, Creative & Comms at Attentive, to talk about what it really takes to build a brand that drives pipeline in a crowded B2B market. Jess gets candid about bringing a hypergrowth org back to its foundation-mission, values, and a point of view people can actually feel. We dig into consent-based personalization that respects customers, why brand and demand aren’t enemies, and how to use AI as a speed-up.We Also ExploreWhy slapping “AI” on your homepage isn’t a strategyHow to make personalization feel human, not creepyBrand vs. demand is a fake fight (and how to prove it)The metric that earns budget: brand health with teeth
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Oct 9, 2025 • 43min

The Truth About Category Creation — and Why Most Get It Wrong with Adam Greco of Hightouch

If your marketing feels harder than it should, you’re not imagining it. So what’s the smarter way forward?In this episode, Adam Greco, Product Evangelist at Hightouch argues for a simpler model: composable CDP. Instead of locking yourself into a monolithic suite, you keep data where it already lives and activate it directly. That means days instead of quarters to get value, and less money wasted on campaigns that annoy customers instead of delighting them. Adam pulls from decades in analytics to show how organizations can finally stop tripping over their own tech, build trust between data and marketing, and focus on the few initiatives that really move the needle.The question: are you doing more, but achieving less?We also explore:Why annual planning done right can be a superpower, not a slog.How to kill the “brand vs. performance” tug-of-war with shared goals.The messy reality of category creation and how not to get steamrolled.Why short-form video is quietly replacing SEO as the new credibility engine.
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Oct 2, 2025 • 48min

Community as a Growth Engine with Sandy Mangat of Pocus

Everyone’s talking about AI, but let’s be honest, most B2B brands still sound like copy-paste corporate speak. The scary part? While you’re stuck writing “safe” content, your competitors are out there building cult followings.On this episode, Jason and Josh talk with Sandy Mangat, Head of Marketing at Pocus, about what it really takes to make people care. Sandy has worked in product, growth, and brand teams, so she’s here to share the lessons you won’t find in a playbook. From building a community people actually want to be part of, to cutting through the AI hype without sounding like a bot, this conversation is all about marketing that feels alive.Here’s what we dig into:Why so many startups crash when product, growth, and brand don’t align.The real secret to category creation (spoiler: it’s not just slapping “2.0” on a slide).How to turn a community from “nice idea” into a genuine growth engine.The fine line between brand personality and just being unclear.Sandy’s one-line marketing philosophy: everything is easier when you’re famous.
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Sep 25, 2025 • 50min

From ABM to Contact-Based Marketing and Building a New Category with Jess Cook of Vector

Marketers are under constant pressure to prove impact. Often with smaller teams and tighter budgets. The challenge? Balancing brand building with demand generation while keeping content fresh and effective.In this episode, Jess Cook, Head of Marketing at Vector, shares how she’s tackling that balance in real time. Jess talks through practical ways to get more value from every piece you create, without burning out your team. She explains why “minimum viable content” can help you move faster, how repurposing can multiply your reach, and why even unexpected moments (like a CEO going rogue on LinkedIn) can become brand building opportunities.We also cover:How to establish authority in a new category.Why repurposing can be your most effective growth strategy.The benefits of testing fast instead of chasing perfection.How to turn unpredictable moments into authentic brand stories.The evolving relationship between brand and demand.
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Sep 18, 2025 • 46min

How Brave Work Actually Gets Approved with Andrew Chen of Hive

When AI can spin up a logo in seconds and templates are everywhere, it’s fair to wonder: why hire a designer at all? Because people don’t connect with “good enough.” They connect with taste, the kind that feels intentional, lived-in, and real.In this episode, Andrew Chen, Head of Brand Design at Hive, makes a simple case: tools help, but taste wins. He talks about how skating and the hardcore scene taught him to make things people actually want, why trust (not slide decks) gets bold ideas approved, and how the next wave favors curators who know what to keep and what to cut. Andrew’s path is a reminder that great work isn’t about pedigree; it’s about context, craft, and caring enough to sweat the details.We also get into:How building trust gets buy-in faster than any moodboard.Using “yes, and” to turn rigid briefs into better ideas.Why juniors shouldn’t wait for permission to pitch the risky thing.How food (seriously) can sharpen your storytelling instincts.
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Sep 11, 2025 • 54min

How to Build Brands That Break the Rules and Win with Scott Smith of Intercom

When everyone’s shouting that they’re “#1 in AI,” how do you actually stand out? Sometimes, the move isn’t a flashy campaign—it’s just saying what you mean, clearly and confidently.This week, we sit down with Scott Smith, VP of Brand at Intercom and the creative mind behind Fin, their new AI agent. Scott speaks about how they built a brand that breaks the rules—ditching rigid style guides for something more like a magazine: expressive, evolving, and full of soul. We talk about what it takes to launch a new brand inside a legacy company, how “boring” billboards became their secret weapon, and why AI isn’t here to steal creative jobs—it’s here to level up the whole game.We also get into:- Why great art direction matters more than ever in an AI-first world- How Intercom reimagined branding as a living, breathing system- Letting go of the “creative genius” myth and building with your team- What it looks like when in-house creative teams run like agencies
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Sep 4, 2025 • 45min

Building Brands People Actually Care About with Steph Bowker of Metaview

With everyone talking about AI, it’s easy to feel like your brand has to shout just to be heard. But sounding like everyone else isn’t the answer, it’s a missed opportunity to connect in a meaningful way.In this episode, we sit down with Steph Bowker, Head of Marketing at Metaview, to talk about what it really takes to stand out in today’s crowded B2B landscape. Steph shares her honest perspective on building brands that feel human, specific, and rooted in real value. We explore what makes people care, how to create a brand that feels lived-in and why thoughtful storytelling (inside and outside your company) might just be your strongest asset.If you’re looking for practical ways to cut through the noise without losing your voice, you’ll want to hear this one.We Also Explore:Why slapping “AI” on your homepage isn’t a strategyHow to turn customers into your most powerful marketing channelWhat makes a real community (hint: it’s not just a Slack group)How smaller teams can punch way above their weight with sharp storytelling
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Aug 28, 2025 • 43min

The Marketer’s Guide to Modern Storytelling with Roman of Sifflet

Maybe it’s not a content problem. Maybe it’s a clarity problem.With AI-generated posts flooding every channel and SEO playbooks changing by the week, B2B marketers are creating more content than ever—yet somehow, it’s hitting with less impact. So what actually sets a brand apart today? It might come down to something deceptively simple: better storytelling.In this episode, Roman, Head of Marketing at Sifflet, shares his thoughtful take on why “90% of marketing is content”—and why we need to rethink how we approach it.We also discuss:Why founder content is peaking—and what comes nextThe quiet return of PR, direct mail, and other "dead" tacticsThe one field in your contact form that tells you what your dashboard never will
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Aug 21, 2025 • 43min

How to Turn Marketing into Entertainment with Chris Cunningham of ClickUp

Everyone’s chasing AI—but what if the real magic in B2B is a rap video, a meme, and two actors with a camera?While most brands stick to safe, polished playbooks, Chris Cunningham is building ClickUp’s marketing like it’s a full-blown media company—and it’s working. In this episode, he takes us behind the scenes of how their small but mighty team racked up 200 million+ impressions by leaning into creativity, comedy, and community.Chris, one of ClickUp’s original team members and now Head of Brand, shares the real (and often hilarious) story of how they went from startup scrappiness to building an in-house content engine that moves the needle. From hiring actors full-time, to turning their content meetings into writers’ rooms, to making rap albums that actually convert.We talk about:The content framework that helps their team test and scale what really worksWhy they bet on humor at the top of the funnel—and what makes it landHow they avoid burnout while making videos every weekThe limits of AI content (and why originality still matters most)What most B2B teams get wrong when they try to “act like media companies”
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Aug 14, 2025 • 55min

Bold Moves That Build Real Brands with Bill Macaitis of SaaS CMO Pro

Let’s be real: most B2B brands are stuck on repeat. Same buzzwords, same bland websites, same tired playbooks. And in a sea of sameness, nobody stands out. So how do you make people actually care?In this episode, we sit down with Bill Macaitis, founder at SaaS CMO Pro. Bill pulls back the curtain on what’s broken in B2B marketing and how to fix it. Spoiler: it’s not another lead-gen campaign or cranking out more content. It’s about building a brand people actually remember.If you’re tired of playing it safe, this one’s for you.We Also Get Into:The secret behind customer marketing that actually drives growthHow to create bold, consistent brand moments without becoming a robotWhy most marketing teams lose trust—and how to win it back

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