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PODCAST

Best Story Wins

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

business marketing

All Episodes

29:13

Building Trust in a Noisy World

Best Story Wins ·

2025/08/07

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

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50:43

Why B2B Buyers Crave Cool, Too

Best Story Wins ·

2025/07/31

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

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41:51

The Quiet Revolution Behind B2B Brand Wins

Best Story Wins ·

2025/07/24

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

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49:32

Meet the Architect of Docusign’s Bold Rebrand

Best Story Wins ·

2025/07/17

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

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24:26

The Anti-Playbook for Modern Brand Builders

Best Story Wins ·

2025/07/10

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 Ann 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

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39:09

The Unscalable Stuff That Scales

Best Story Wins ·

2025/07/03

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

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42:05

Why Trust Is the New Brand Currency

Best Story Wins ·

2025/06/26

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

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47:24

Becoming Marketing’s Big Sister

Best Story Wins ·

2025/06/19

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

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44:50

Your Brand Doesn’t Need a Makeover

Best Story Wins ·

2025/06/12

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

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39:07

Why Most GTM Plans Don’t Work

Best Story Wins ·

2025/06/05

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,

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37:19

Why Most Agencies Are Failing Modern Marketing Teams

Best Story Wins ·

2025/05/29

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

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34:22

Marketing’s Next Revolution Is Human First

Best Story Wins ·

2025/05/22

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

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40:00

Why Most B2B Strategies Are Built on a Broken System

Best Story Wins ·

2025/05/15

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

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41:54

Can CMOs Take Back Control of Growth?

Best Story Wins ·

2025/05/08

Marketing leaders are under more pressure than ever, and many are stuck playing defense. With budgets tightening and short-term wins taking priority, how can CMOs reclaim their seat at the table and drive real business impact?In this episode of Best Story Wins, Michael Duda—partner at Bullish and former agency leader—shares how he’s blending creative and financial capital to back high-growth brands like Peloton, Warby Parker, and Harry’s. He explains why marketing should be treated as an investment,

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37:21

Trust Is the New Growth Hack w/ Chase Howell

Best Story Wins ·

2025/05/01

Marketers are pumping out more content than ever, yet consumers somehow trust it less than their own data. Impressions are meaningless if you’re not driving impact. In this episode, Chase Howell, VP of Marketing at InfoTrust, shares the formula of B2B marketing that builds trust, converts, and scales without losing its human touch. From launching bestselling books to ditching digital-only in favor of in-person events, Chase shares what it takes to make your brand unforgettable in a landscape

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53:03

How to Build a Billion-Dollar Story w/Ben Parr

Best Story Wins ·

2025/04/24

Today, anyone can build an AI product on a weekend. To stand out in the market, you must rely on your story. In this episode, we are joined by Ben Parr, co-founder of Octane AI and Theory Forge Ventures to talk about what separates good companies from great ones: story and speed. Drawing from past experiences building AI products (before LLMs existed), Ben shares insights on how startup founders should think about brand, content, competition, fundraising, and the marketing industry post-ChatGPT. We

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56:46

How Smart Founders Use AI to Win w/ Hiten Shah

Best Story Wins ·

2025/04/17

Today, thinking about AI completely replacing humans is impossible. Why? Because it means replacing creativity, context, and more importantly, intuition. Hiten Shah, serial entrepreneur, investor, and now working on AI at Dropbox, joins Josh and Jason to discuss how smart marketers and builders are using AI as a thought partner rather than a content machine. Hiten also drops hard-earned wisdom on what marketing still gets wrong, why engineers still (and will likely always) lead the startup ecosystem

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46:11

Creating Content People Actually Care About w/...

Best Story Wins ·

2025/04/10

If your content doesn’t have a ‘so what,’ you shouldn’t bother hitting publish. Drew Evans, who leads B2B content strategy at Notion, joins the show to talk about why storytelling—not templates, tools, or tired SEO tactics— moves the needle in B2B marketing.Drew makes a strong case for substance over spam by emphasizing the importance of a great writing comeback. He gets candid about what’s broken in B2B and what marketers need to prioritize instead.We also explore:Why traditional blog content is

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42:24

The CMO Playbook for the AI Era w/ Gabe Larsen

Best Story Wins ·

2025/04/03

If your brand only shows up when a customer has a problem, you’ve already lost the game.In this episode, we sit down with Gabe Larsen, CMO of Kustomer, to tear into what most B2B marketers are getting wrong, and why brand isn’t a “nice to have,” function but rather the differentiator. Gabe drops the kind of no-fluff, first-principles manifesto that B2B leaders need to hear right now: customer service starts at hello, not help.We break down:Why “AI-powered” means nothing if your messaging isn't good

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35:58

Ep. 69 Megan Brunner of Adobe

Best Story Wins ·

2025/03/27

B2B marketing doesn't need to be predictable or stale. As people’s attention span is shrinking, shouldn’t B2B content be as vibrant and creative as consumer-focused storytelling?In this episode, Megan Brunner, B2B Content Strategist at Adobe, reveals how brands can level up their storytelling, infuse genuine creativity into their content, and move beyond traditional corporate imagery by applying the best from B2C content strategies. Megan's unique career path from action sports to working at some of

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109 results

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