Best Story Wins

Hosted by Column Five

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131

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Jun 2026

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About the show

Welcome to “Best Story Wins,” a podcast for marketing and branding professionals looking to unlock their growth potential. Hosted by Column Five—a B2B marketing agency that specializes in brand and content marketing for SaaS companies—each episode features insightful conversations with industry leaders who are winning customers’ hearts and minds by building world-class brands. Tune in to hear expert insights, hard-won lessons, and key strategies to take your own marketing efforts to the next level.

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June 11, 2026Episode 13049 min

Stop Measuring Brand Like a Performance Channel with Bill Kenney from Focus Lab

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 ROI behaves like going to the gym — you don't step on the scale the morning after — and that the real opportunity for agencies isn't using AI to ship work faster, it's handing clients the tooling to run their own brand without you in the room. He also says the quiet part out loud about why a weekend in an AI tool will never replace what actually happens inside a 16-week rebrand: the second-guessing, the cold feet, the "can we sit on this another week."We also cover:The Apple test for why feature parity just turned product differentiation into a branding problem, not an engineering oneWhy he shut down his own sub-agency after realizing clients "don't give a shit" how big or small your other clients areThe one belief he died on for years — that a brand has to launch in a single perfect moment — and why he now thinks a slow, slightly messy rollout works fineThe first-meeting question he asks every CEO that quietly decides whether the whole project survives

June 4, 2026Episode 12737 min

Why Nobody Trusts a Brand They Just Met with Amit Singh

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, and Nintendo — long enough to watch "dot-com" go from billboard flex to embarrassing relic, and he's convinced AI is headed the exact same way. His argument: the companies sprinting to rebrand as AI companies are mortgaging years of earned trust, while the question that actually decides whether you survive — why should you exist? — goes unanswered in most boardrooms. He maps where AI earns its seat at the table, where it quietly wrecks your creative without anyone noticing, and why the people declaring storytelling dead are reading the wrong scoreboard.We also cover:A Meta study found AI-generated copy matches or beats humans on sub-$100 products — and consistently *loses* on anything pricier, where emotion does the selling. Most teams are pointing it at exactly the wrong work.Nintendo doesn't make video games. It makes smiles. Why your reason to exist is the North Star you build against — and the one thing you'll never put in an ad.88% of marketers have adopted AI. Adoption was never trust — and Amit thinks the gap between the two is where the real risk is hiding.Long-form is quietly back: why a five-minute Adidas film outperforms your six-second TikTok precisely *because* attention has never been scarcer.

May 28, 2026Episode 12643 min

The Irreducible Part: Taste, Judgment, and the Stories Machines Can't Tell — with Julianne DeVincenzo & Dan Reid from Optimizely

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 people deep inside one of the most interesting rebrands happening in B2B right now. They make the case that the real threat of AI isn't job replacement — it's the slow erosion of judgment, taste, and the willingness to make someone uncomfortable. Julianne and Dan talk about how they're rebuilding Optimizely's content engine from the ground up, why they're turning their own marketers into subject matter experts and journalists, and where they're drawing the line between what AI can own and what stays irreducibly human.We also cover:• Why the volume-as-strategy era is producing content that 'passes through people like water through a screen' — and how Optimizely is deliberately building against that.• How Dan is working directly with engineers to teach their own AI to honor brand — including the surprisingly simple feedback that blew a senior engineer's mind.• What happens when you empower employees to use AI and wake up to find your unreleased brand assets have already been fed into someone's personal workflow.

May 21, 202647 min

Clarity Wins: Why Taste Can't Be Prompted with Mathew Barnes of IBM

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 about all of it.In this episode, Josh and Ross sit down with Mathew Barnes — brand leader at HashiCorp, now IBM after two consecutive acquisitions — to pull apart what actually makes brand work at scale. Mat makes the case that AI will expose every creative who doesn't know what good looks like, and that clarity isn't a buzzword: it's the only thing that's ever made any brand matter.We also cover:•Why AI will 'expose the hell out of you' if you don't already know what great looks like — and what taste actually is when you can't fake it•The one question every brand and creative team skips that causes every siloed, inconsistent campaign — and how Matt's team asks it before anything gets made•What it actually feels like to lead brand inside a 100-year-old institution — and what IBM's design sophistication taught a startup veteran who thought he'd seen everything

May 14, 202629 min

The Death of the Keyword — And What Comes Next with Hadassah Pegado Dalisay of Outreach

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, Head of Content Strategy, SEO, and AEO at Outreach — the agentic AI platform for revenue teams — who has spent over a decade watching the search game change and finally break. Hadassah makes a case that will sting a little: the old keyword-volume playbook didn't just stop working, it actively made you worse at the thing that actually matters — being the trusted answer when a buyer asks an AI what to buy. Her fix isn't to abandon SEO. It's to collapse the wall between SEO, content strategy, and revenue intelligence into something that actually earns attention.We also cover:•Why mining your own sales transcripts is the most underrated content research method in B2B — and how Outreach does it at scale every quarter•The difference between signal-driven and keyword-driven content strategy, and why the companies chasing volume right now are building a liability, not an asset•How to make the case inside your org that AI visibility isn't a marketing metric — it's a pipeline metric

May 7, 2026Episode 12249 min

In the AI Age, Taste Is the Last Moat with Avi Ashkenazi of Deel

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 are expected to unblock themselves — breaks down what actually separates designers who thrive in high-velocity environments from those who flame out. He makes the case that taste, devotion, and the willingness to stay opinionated are what AI can't automate, and explains why "vibe coding" will always hit a wall the moment a client asks for something exact.We also cover:Why Deel built a "Delight" team — and what it tells you about the ROI of caring about the emotional texture of your product, not just its functionalityThe agentic design system Deel is actively building, where interfaces construct themselves on demand and no two users ever see the same pageHow to run a 120-person distributed design org with no office and quarterly themes that actually move everyone in the same direction

April 30, 202645 min

The Secret to Building Products People Fall in Love With with Jon Howell of Ramp

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 building right now. Jon makes the case that brand and product design aren't two lanes on the same highway; they're an infinity loop that feeds itself. He breaks down what it takes to actually build the connective tissue between those two worlds — not as a philosophy, but as a daily practice of shipping fast, reading the room, and sweating the details before the PM moves on.Also in this episode: • Why the "we'll polish it next cycle" myth is quietly degrading your product — and what to do before the engineer ships and moves on • How AI is making brand design more efficient and more generic at the same time, and the discipline required to use it without losing your point of view • The interpersonal moves that actually break down silos between brand and product teams — before you ever show up

April 23, 2026Episode 12346 min

The Force Multiplier Most B2B Brands Are Ignoring with Ryan Hammill of ServiceNow

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 creative effectiveness scores — not by chasing flash, but by getting ruthlessly clear on what a human being actually feels when they choose enterprise software. He makes the case that cutting the B2B bullshit isn't an aesthetic choice: it's a revenue strategy. From Idris Elba to Notorious B.I.G. to the moment Taylor Swift's kiss cut to his AWS spot, Ryan explains how humanizing invisible technology at scale actually works.Bullet PointsWhy the Fernando Machado 6-to-1 multiplier argument should change how every CMO thinks about creative risk — and why most don't let itHow ServiceNow's character-driven campaign structure borrows more from The Office than from enterprise SaaS playbooksThe brand-vs-demand false binary: what Airbnb's ad spend restructure teaches B2B companies about search efficiency and brand gravityTimestamps:0:42 Introduction & Ryan's Background1:31 From Agency to Tech: The Career Journey5:50 ServiceNow's Bold Brand Identity8:53 B2B Storytelling: Cutting Through the Jargon18:24 Risk-Taking and the Two-Way Door Mentality21:10 The AWS NFL Campaign: A Case Study26:14 AI, Buzzwords & Authentic Messaging31:39 Brand Building vs. Demand Generation38:19 The Emotional Intelligence of B2B Buyers41:18 Proudest Work & What's Next

April 16, 2026Episode 12249 min

Stop Catching Up. Start Doing Something with Asher Rumack of C5

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 that AI is a shortcut and rebuilding it as a craft. Asher makes the case that creative, strategy, and marketing have never been three different jobs, and that the agencies still pretending otherwise are going to feel it. He also breaks down why AI search is the most underpriced channel in B2B right now — and why most brands are showing up in it completely wrong.We also cover:Why 'catching up with AI' is a trap — and the mindset shift that actually makes the tools usefulThe specific reason your LLM search presence is probably lying to your buyers right now (and the low-effort fix)Why the wild idea in the pitch deck is about to become the default — and what that means for how agencies price creative risk

April 9, 202657 min

The AI Shortcut That Backfires Every Time with Jason Lankow from C5

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 obsesses over speed and scale, Jason makes the case for something far less sexy (but far more critical): governance at the moment of creation. We dig into what it really takes to build a “brand operating system”—one that doesn’t just sit in a dusty PDF but actually shows up inside the tools your team is using every day. From eliminating brand drift across AI-generated content to making your messaging machine-readable (yes, really), this episode is a wake-up call for anyone still treating AI like a shortcut instead of infrastructure.We also explore:Why “just use AI” is the most dangerous mandate in B2B right nowThe real reason your brand is becoming invisible in AI search (AEO)How to scale content without turning it into generic sludgeWhy taste—not tools—is your last unfair advantage