Best Story Wins

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.

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.

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

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

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

It’s a tough time to be a marketer. Teams are lean, expectations are high, and AI is everywhere—but automation can only take you so far if your brand voice gets lost in the shuffle. So how do you keep your storytelling sharp and human in a world that’s increasingly not?In this episode, we’re joined by Trish Seidel, Marketing Director at Teal and the voice behind “Marketing’s Big Sister.” Trish brings a thoughtful, grounded perspective on what it means to build real brand connection in a noisy landscape. From her experience bridging U.S. and European startup cultures to her experiments with AI-powered content, Trish shares what’s working, what’s broken, and why marketers deserve better.We also talk about:Teal’s unique approach to scaling content with AI agents (that still sound human)The cultural divide in startup marketing across continentsWhy ABM often misses the markThe emotional weight of proving your value in scrappy teams

Brand teams are obsessed with differentiation, but what if distinctiveness is the real power move? And while you're chasing loyalty, your competitors are winning with reach.In this episode, Matt Maynard, Asana’s Head of Brand and Advertising, joins the show to challenge the dogmas of B2B brand strategy. From calling out the cult of rebrands to exposing the limits of loyalty and the illusion of celebrity endorsements, Matt lays out a new playbook rooted in evidence. He unpacks how real brand growth comes from building mental availability, not just big ideas, and why most marketers still mistake folklore for fact.We dive into:Why most B2B brand teams are optimizing for creativity instead of outcomesThe distinctiveness vs. differentiation smackdown (and why it matters more than ever)How AI is the ultimate sparring partner—not just a creative sidekickWhy brand characters beat celebrities in the long game of memoryHow Asana is automating workflows to bring brand science into every touchpoint

Many go-to-market strategies sound good on paper but fall apart in practice. The issue isn’t the lack of talent, but rather the misalignment, timing, or wrong assumptions they’re founded on.In this episode, Brandon Redlinger, fractional marketing leader and co-founder of The Forge community, shares what he's learned from years in the trenches of B2B marketing, from building ABM categories to launching his own curated community for marketing leaders. He talks about why brand matters more than ever, what makes community-building actually work, and how to avoid the common pitfalls that derail go-to-market efforts.We also explore:Why category creation starts with clarity, not buzzwordsThe value of brand in speeding up pipeline and reducing CACHow community can elevate marketing leadership—not just audience engagementWhat early-stage companies must get right in their GTM motionHow marketing leaders can vet roles and align with CEOs from day one

The old agency model is broken, and smart brands aren’t waiting around to fix it. Instead, they’re building lean, strategic ecosystems where storytelling, rather than scale, is the engine that propels growth.In this episode, Harrison Iuliano, cofounder of Moving You to BCC, breaks down why the classic agency-client model is officially dead and what smart brands are doing to replace it. He shares how high-performing brands are creating modern marketing machines by blending fractional talent, curated creative partnerships, and brand-first thinking. We dive into:Why brand, not performance, is your most defensible assetHow to structure your team for speed, quality, and creative outputWhat most companies get wrong about agency selectionWhy great products don’t save bad brands—and vice versa

The brands that move first on human connection build an edge no algorithm can touch. The question is: Will you move fast enough to matter?In this episode, Allison Stadd of Shipt lays out why brands that lead with care, and not only convenience, are the ones winning now and leading the human-centric revolution in marketing. She breaks down how human connection is becoming the real growth engine, how collapsing old brand and performance silos is unlocking smarter strategies, and why micro-communities are the future of loyalty.We also discuss:Why cultural activation is the new brand foundation.How customer anecdotes can turn into an untapped growth channel.Why every brand needs a drummer mindset to lead from the back and still own the stage.

Most B2B marketers are stuck proving short-term wins. Not because it drives the best results, but because it’s the only story the numbers can tell. Could this be why long-term growth, brand equity, and strategic influence keep slipping through the cracks?In this episode, Victoria Gamlen, CMO of Boundary Analytics, unpacks the disconnect between brand investment and how we measure success. She explains why traditional attribution models fall short in B2B, how correlation and time lag analysis offer a clearer view of pipeline impact, and what marketing leaders need to rethink to align with how buyers make decisions today.We also discuss:Why “brand vs. demand” is a false choice—and what to focus on insteadHow to use high-intent inbound as a bridge between brand activity and business outcomesWhat’s behind the recent shift in how leading companies approach brand marketingHow to advocate for brand investment with data that resonates with the C-suiteThe biggest gaps in B2B marketing measurement—and how to fix them