Best Story Wins

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

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”

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

We’re creating more content than ever—but at what cost to meaning and connection?In this episode, Kelly Phillips—VP of Brand Marketing at Faire, and former brand leader at Airbnb, YouTube, and Google—shares what it really takes to build a brand that people trust and feel connected to.We talk about what makes brand matter in the age of AI, how to build trust on both sides of a marketplace, and what it looks like when your brand actually helps people succeed—not just sells to them.We also discuss:Why Faire wants to be a partner, not just a platform, for small retailersThe “Fair Forecast” and the power of data-driven, non-boring trend reportsWhy early brand investment is no longer optional for AI-first companies

If your brand doesn’t spark a feeling, it’s already forgettable. In a world where every product looks the same, the only thing that truly sells is vibe.B2B marketing is broken. Everyone’s selling the same tools with the same bland copy—and in the AI era, product parity is only getting worse. So how do you stand out when sameness is the default? You build a brand people actually feel something about. In this episode, Kevin Branscum, VP of Brand Marketing at Typeform, breaks down how to inject personality, culture, and staying power into your B2B brand.We also discuss:Why most B2B brands sound like AI wrote them—and how to sound human againHow to borrow from the playbooks of fashion and luxury to build worlds, not just marketing campaignsHow to think beyond spreadsheets and bring real people—your customers and their customers—into the heart of your marketing

Too often, B2B brands chase clicks that don’t lead to real results. The fix? It’s not more ad spend—it’s aligning your systems and strategy.In this episode, Deanna Adams, Senior Director of Integrated Campaign Marketing at Dropbox, reveals how to actually make your brand show up across the entire customer journey—not just in a 15-second pre-roll.Deanna shares how her team re-engineered Dropbox’s content engine for agility, built emotional resonance through integrated campaigns, and created a structure that lets the brand promise echo from awareness to advocacy. It’s not theory—it’s game film from the frontlines of modern B2B marketing.We also cover:Why the “brand vs. performance” debate is holding your team backHow AI is shifting from shiny feature to workflow essentialWhat a truly integrated customer journey looks like in practiceHow to structure agile teams that actually collaborate

Great brands don’t just evolve—they outgrow their origin stories.Docusign made the signature famous. Now it’s on a mission to make agreements iconic—and that meant blowing up the brand as the world knew it.In this episode, Carla Weis, VP of Brand and Creative at Docusign, shares the bold, strategic, and fast-paced four-month overhaul behind one of the most successful B2B rebrands in recent years. We dive into how Carla’s team transformed the 22-year-old brand into a full-blown intelligent agreement platform—and why that required more than just a new logo.We also discuss:The business risk of staying visually familiar when your product leaps forwardWhy B2B brand archetypes aren’t fluffy—they’re functional decision-making toolsHow “self-serve creative” and 600+ Canva users are scaling the brand with precisionWhy they embraced jargon, dropped the “everyman,” and leaned into the Sage-Ruler-Hero brand trio

If your brand feels more like a dusty whitepaper than a bold statement, you're doing it wrong.In this episode, we sit down with Emily Anne Epstein, the content lead behind Sigma’s rapid rise. Emily unpacks why every modern brand needs a POV that punches—and how to create a system where thought leadership isn’t just encouraged, but expected. She shares why content is the engine, not the accessory; how to weaponize data to justify bold creative bets; and what it really takes to stand out in a sea of same.We also coverWhy purity tests for AI content are a dead-end distractionHow Sigma uses attribution data to justify every content decisionWhy you don’t need a Head of Brand to have a killer brandThe real secret to scaling thought leadershipHow to inject “punk rock” into your B2B tone without losing credibility

Tech is moving fast. But trust? That’s still built the old-fashioned way.As AI reshapes how we work, connect, and build, the brands that will win aren’t the ones shouting the loudest—they’re the ones people actually believe.In this episode, Ross Mayfield—Head of Product for Workplace AI at Zoom—joins us to talk about why the future of marketing isn’t just smarter tech, it’s deeper human connection. Ross has seen how product, brand, and culture intersect—and how AI is forcing us to rethink it all.If you're trying to stand out in a market where everything’s automated and nothing feels real—this one’s for you.We discuss:Why your product experience is now your brand’s loudest voiceThe return of trust as the most powerful growth strategyHow agentic AI is turning meetings into momentumWhat most startups get wrong about scale (and what to do instead)Why integration is becoming a commodity—and what that means for differentiation

While many fintechs are focused on surface-level features, Ethan Bloch is building an ambitious, AI-powered financial product from the ground up. In this episode, Ethan, Founder of Digit and now Hiro Finance, shares why he believes most financial tools are more cosmetic than useful, and how a truly helpful product can speak for itself—no referral codes needed. He breaks down how AI is unlocking more personalized financial support, why trust is the most valuable asset in fintech, and how strong branding often follows when you genuinely solve real problems.We also cover:How building in the age of large language models reshapes teams, trust, and timelinesWhy putting product value first creates long-term brand strengthThe single survey question that reveals true product-market fit