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Best Story Wins

Best Story Wins

Written by: Column Five
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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.Column Five Careers Economics Leadership Management & Leadership Marketing Marketing & Sales Personal Success
Episodes
  • Beige Is What Happens When Nobody's Brave Enough to Be Wrong with Sonja Silveira of Cisco

    Beige Is What Happens When Nobody's Brave Enough to Be Wrong with Sonja Silveira of Cisco
    Jul 2 2026
    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 means the marketers using them need more suspicion, not less. She also names the thing most B2B brands won't say out loud — they all sound the same now, AI just sped up the slide into sameness, and the fix has nothing to do with the tools.We also cover:
    • Why treating AI like "an answer machine" is the fastest way to lose your edge — and what to check before you trust a single stat it gives you
    • The real reason beigefication isn't new, why it's "safe," and why safe is exactly what's killing your content
    • Why almost every B2B brand that tries to become a media company hits the same wall — and what Cisco's Story Lab is doing differently
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    48 mins
  • AI Made Brand the Only Thing Left That Matters with Adam Morgan of Twilio

    AI Made Brand the Only Thing Left That Matters with Adam Morgan of Twilio
    Jun 25 2026
    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 palettes before they've earned the right to, and why brand resurgence isn't a reaction to AI fear — it's AI's actual byproduct. When everyone can generate a slick landing page for free, the thing AI can't fake becomes the whole game.We also cover:
    • Why Adam built Twilio's entire rebrand around a single emotional truth he found at Hearst Castle — not a brand workshop
    • The real reason AI is making brand storytelling more valuable, not less, and why "AI-resistant content" is the new differentiator
    • Why locking creatives into rigid brand guidelines backfires, and what a "systems approach" looks like instead
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    49 mins
  • Taste Is the Only Thing AI Can't Generate (Yet) with Matt Scribner of Atlassian

    Taste Is the Only Thing AI Can't Generate (Yet) with Matt Scribner of Atlassian
    Jun 18 2026
    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 pitch for the tools or a doomsday headline about job loss. It's something more useful: an honest account of where AI actually helps, where it quietly fails, and why the designers who thrive won't be the ones who prompt the best.

    We also cover:
    • AI can get you to 60% — but if you couldn't get past 60% without it, you're not getting past it with it either
    • We're heading toward a "singularity of design" where everything starts looking the same, and the only antidote is taste you built before the tools existed
    • The Arts and Crafts movement followed the Industrial Revolution for a reason — and the same correction is coming for brand
    Show More Show Less
    38 mins
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