Best Story Wins

Every designer you know is quietly panicking about the same thing: their Figma hours dropped from 90% of the week to 30%, and nobody told them what to do with the other 60%. Is that a crisis or a promotion? Maria Irie runs brand at Chili Piper with a team of two — and she's spent the last year rebuilding her entire job around AI without losing what makes the brand feel human. She's mid-migration f...

Every AI tool you use was built to keep you happy, not to make you right. That's a problem when "happy" is also the fastest route to content nobody remembers. Sonja Silveira has run content teams at Meta, athenahealth, and now Cisco , and she's done with the idea that AI is either a job-killer or a magic answer box. Her real argument: these tools are optimized for engagement, not accuracy, which m...

Twilio used to read like a company built for developers and nobody else. Then it found one word that made every audience feel like they belonged to the same tribe. Adam Morgan , VP of Brand and Creative at Twilio , spent three months finding that word  "builder" and watched it turn a stalled rebrand into what he calls lightning in a bottle. He explains why most companies chase logos and color pale...

Every brand team is being handed AI tools and told to do more with less. What they're not being told is that without taste and a real idea, the output is just sophisticated noise at scale. Matt Scribner is a growth designer at Atlassian — a company whose brand touches tens of thousands of visitors a week — and he's been inside the AI-enabled design workflow longer than most. His take isn't a sales...

Every quarter, someone asks you to prove the rebrand paid for itself in dollars. Bill Kenney's answer after 16 years: you're measuring the wrong thing, and the spreadsheet was never going to save you anyway. Bill built Focus Lab into one of B2B's sharpest branding shops by owning a single vertical back when everyone warned him that niching down would scare off clients. He makes the case that brand...

You're being outshouted. The average person now absorbs 5,000+ messages a day and reaches for their phone 205 times — and the industry's big answer was to staple "AI-powered" onto the homepage and call it a repositioning. That's not building a brand. It's a withdrawal from the one account you can't overdraw. Amit Singh has spent three decades building brands at Adobe, American Express, Starbucks,...

Most marketing teams are drowning in output and starving for meaning. The more they feed the machine, the more the machine becomes the creative director — and somewhere in the noise, the person on the other end of the content stopped mattering. In this episode, Josh and Ross are joined by  Julianne DeVincenzo , Head of Content Strategy, and Dan Reid , Creative Director — both at Optimizely — two p...

Every week, another round of tech layoffs gets explained away with the same two words: artificial intelligence. Meanwhile, the people making those calls have never once asked whether the cuts make strategic sense — or whether they're just making a number go up. Mat Barnes has been building brands for 30 years, survived two back-to-back acquisitions, and now leads brand at IBM . He has opinions abo...

Your SEO traffic is up. Your pipeline is flat. Something broke, and it's not your team — it's the entire model most B2B marketers were trained on. The buyers who used to find you on Google are now getting their shortlists from ChatGPT, and if you're not in that conversation, you're invisible at the exact moment it matters most. In this episode, Josh and Ross sit down with Hadassah Pegado Dalisay,...

While B2B companies debate whether to "embrace AI," one of the fastest-growing HR platforms in the world is already asking its designers to ship production code, run their own research, and rethink what a UI is in the first place. In this episode, Avi Ashkenazi — Senior Product Design Director at Deel , where 97 product designers work without a physical office, operate directly with the CEO, and a...

Most brand teams talk about blurring the line between brand and product. Jon Howell has spent a decade actually doing it — at Twitch, Lyft, Robinhood, Dropbox, and now Ramp. There's a reason that line keeps surviving: most companies aren't set up to erase it. In this episode, Josh and Ross sit down with Jon Howell, who leads brand experience design at Ramp — one of the fastest-moving fintechs buil...

B2B marketing keeps asking why it can't earn the same attention as consumer brands — then keeps writing copy that reads like a product spec sheet. The problem isn't the category. It's that most enterprise marketers confuse explanation with storytelling and call the result strategy. Ryan Hammill, Creative Director at ServiceNow has built campaigns that ran post-Super Bowl and earned 99th-percentile...

Most B2B marketing teams are sprinting to adopt AI and landing in exactly the same place they started — more content, same forgettable results. The problem isn't the tools. It's that nobody stopped to ask what actually needed to change before reaching for them. In this episode, we sit down with Asher Rumack — Column Five's VP of Creative Strategy — who has spent the last year dismantling the idea...

Everyone’s pumping out content at scale—but it all sounds like it came from the same intern with a chatbot. So here’s the real question: if AI is doing the writing, who’s actually steering the story? In this episode, Column Five co-founder Jason Lankow breaks down the uncomfortable truth most B2B teams are avoiding: AI isn’t a content problem—it’s a brand system problem. While everyone else obsess...

AI isn’t replacing your team. It’s exposing how replaceable your thinking is. Everyone’s obsessed with speed—but no one’s talking about the real problem: mediocre work at scale. So what’s actually happening here… is AI making you better, or just faster at being average? In this episode, Josh sits down with  Julien Palliere , Business Development Lead at Column Five to unpack how we cut through the...

In a world flooded with AI-generated noise, most B2B brands are still treating social like a billboard—when it’s actually the front page of their brand. In this episode, Jacqui Morgan, breaks down why most content gets ignored and what it really takes to earn attention, build trust, and drive results. We get into why social is a business driver (not a support channel), why chasing the algorithm is...

Google used to be your gatekeeper. Now an AI can summarize your entire category… and forget your brand exists. In this episode, Lexi Croisdale Director of Global Content Marketing at Varonis breaks down what happens when search stops being clicks and starts being answers. We talk about why the old SEO playbook is getting cooked by AI discovery (AEO/“AI search”), and how B2B teams need to shift fro...

If your product isn’t in the protected AI budget line, you’re about to become an “optional tool” with a UI. In this episode, Julien Sauvage CMO at Cordial delivers the reality check B2B teams don’t want—but need: the AI wave isn’t just changing how software gets built, it’s changing where money goes. And if you’re still running marketing like it’s an infinite-seat-count world, you’re basically try...

If your B2B “strategy” is still a funnel diagram and a stack of specialists, you’re not building growth — you’re maintaining a bureaucracy with a logo. In this episode, Devin Bramhall , Fractional Chief Growth Officer delivers the uncomfortable truth most teams avoid: B2B companies don’t fail because marketing “needs to do more.” They fail because the funding model doesn’t fit the moment… and the...

If your content marketing strategy still depends on gated PDFs and vanity metrics, you’re basically shouting into a void and calling it demand gen. In this episode, Matt Hemsley , Marketing Operations Team Lead at Asana delivers the unsexy truth: the funnel isn’t “broken”—it’s been replaced. He breaks down what happens when AI becomes the new front door, web traffic gets weird, and attribution sta...

Search isn’t broken—it’s been replaced. Buyers are skipping funnels, ignoring gated PDFs and asking AI to decide who’s credible before they ever talk to sales. If your content still assumes attention is linear, you’re not behind—you’re irrelevant. In this episode, Amanda Verdino , Director of Content Marketing at Forma dismantles the comfortable lies B2B marketers tell themselves about storytellin...

Search is decaying, attention is fragmented and AI is rewriting the rules faster than most teams can update their decks. If you’re still planning content like it’s 2019, you’re already invisible. In this episode, Kyle Denhoff , Sr Director of Marketing at HubSpot , pulls the curtain back on what happens after the inbound era. We get brutally honest about why channel-first thinking is dead, how Hub...

AI proof isn’t “building trust.” It’s getting ignored—or worse, backfiring—because it’s generic, gated, and wildly irrelevant. In a world of risk-averse buying committees and AI-driven discovery, your “best case study” might be your biggest liability. In this episode, Jillian Hoefer (Head of Content at UserEvidence ) delivers the reality check B2B teams keep dodging: buyers don’t need more claims—...

Your brand content isn’t “showing up.” It’s getting summarized, re-ranked, and sometimes straight-up misrepresented by AI—and your pipeline won’t tell you why. In a world where buyers ask ChatGPT first, the homepage isn’t your front door anymore. The chat box is. In this episode, Kevin White (Head of Marketing at Scrunch ) delivers a much-needed reality check on AI Search: there are no true “exper...

Your brand content isn’t “scaling.” It’s getting cloned into beige mush by AI—and your buyers can smell it. In a world where everyone can publish 10x more, “more” doesn’t win. Better wins. In this episode, Jessica Rosenberg (Head of Brand at AirOps ) delivers the reality check B2B teams keep dodging: AI doesn’t make marketing magically faster—it makes mediocre faster. Jessica unpacks why AI search...