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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

46:44

Taste as a Secret Weapon with Jeff Stark of Suki AI

Best Story Wins ·

2026/01/08

Your brand isn’t losing to “faster” AI teams. It’s losing to the ones protecting their humanity. As generative tools flood feeds with beige, lookalike creative, the real threat isn’t robots—it’s your team quietly lowering the bar. Are you using AI to unlock better ideas…or to justify shipping forgettable work faster?In this episode, Jeff Stark, Head of Creative at Suki AI, gets brutally honest about what AI can’t do: develop taste, earn trust, or build a point of view. He shares how Suki—an AI

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56:57

How to Increase Brand ROI Through Scale, Speed, and...

Best Story Wins ·

2026/01/02

Your brand isn’t losing to competitors, it’s getting flattened by “good enough.”In a world where AI can generate passable B2B content in seconds, bland isn’t safe. It’s fatal.In this episode, Dan Schwer of Rippling breaks down what brand actually looks like inside a 6.000-person SaaS company with a creative team of 15. We go straight at the uncomfortable stuff: why “brand vs. demand” is a lazy (and expensive) debate, how a brand refresh becomes a business lever (not a design hobby), and what it

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40:07

The Bold Bet Smart CMOs Are Making in 2026 with...

Best Story Wins ·

2025/12/18

Your brand isn’t losing to competitors, it’s drowning in “helpful” content no one remembers. In an AI-everywhere world, bland is broken and volume is just a faster way to disappear.If LLMs can write what you ship in 10 seconds, why would a buyer choose you?This week, Sylvia LePoidevin delivers the reality check B2B marketers have been dodging: content volume is a commodity, brand is the moat. We dig into how AI-native teams actually work (tastemakers and operators), why “helpful” guides are table

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50:36

SEO, AEO, and the Return of Good Marketing with Jenna...

Best Story Wins ·

2025/12/11

Your brand isn’t losing to competitors, it’s getting ghosted by the algorithm. As AI eats search, the “spray and pray” content playbook turns invisible. Are you training the models…or training your team to burn cash?This week, Jenna Hannon, Founder & CEO of Hatter, drops a State of the Union that B2B marketers need to hear: SEO isn’t dead, AEO (AI Engine Optimization) is here and lazy tactics are DOA. We unpack why LLMs reward actual marketing (crisp messaging, specific content, real PR) and

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52:24

Ditching Best Practices: How Courageous Brands Get...

Best Story Wins ·

2025/12/04

Your funnel isn’t broken, but your nerve is. “Best practices” are just average practices with better PR. If every headline, homepage, and hot take sounds the same… what’s the one bold move that makes you unforgettable?In this episode, Udi Ledergor, Chief Evangelist at Gong and author of Courageous Marketing, torches the safe playbook and helps us build a braver one: a sharp, differentiated POV that slices through “sea of sameness” B2B. We get brutally practical on how to stop shipping beige content,

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63:21

Tomato Sauce and the Stories Behind What We Buy with...

Best Story Wins ·

2025/11/20

Marketing is drowning in AI sludge, vanity dashboards, and “spray and pray” content. Your brand is getting lost, not because your product is weak, but because your taste is.In this episode, we sit down with Andrew Lee, Partner Marketing Leader at Microsoft, to torch the illusion that more content equals more impact. Together, we unpack why “brand vs. performance” is a fake fight, why taste is the last unfair advantage, and how to build owned distribution that survives algorithm mood swings. Your CMO

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50:41

The Feeling of Knowing: Brand in the Age of LLMs,...

Best Story Wins ·

2025/11/13

LLMs are already “deciding” your brand for buyers. Are you shaping that story or letting the machine write it? If your marketing still sounds like everybody else’s, congratulations: you’ve trained the models to ignore you.This week we rip into the hottest B2B reality: AI Engine Optimization (AEO) meets human-only brand. Ari Yablok, head of brand at Island, shows how to beat sameness by sending clear “this is new” signals, building experiential brands that people feel (not just read), and using

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53:31

Everything’s Changing: How Smart CMOs Stay Ahead with...

Best Story Wins ·

2025/11/06

Budgets are shrinking, patience is thinner and the CMO seat is a revolving door. Keep playing the old playbook and you’re next.What if the path forward isn’t “more content, faster”, but a hard reset on power, process and what we even call “brand”?In this episode, Drew Neisser, Founder of CMO Huddles, drops a reality check on B2B: CMOs are operating in Antarctica—hostile, short-term, and PE-pressured and it’s still the most exciting moment in marketing. We get blunt about the “do more with less” lie,

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43:50

Story Is the Moat: How to Build One at Scale with...

Best Story Wins ·

2025/10/30

Everyone’s racing to “do more with less,” then wondering why everything sounds the same. Budgets shrink, headcount drops, and the AI mandate lands like a memo from Mount Olympus: use it, ship faster, cut costs. Here’s the plot twist: AI isn’t your edge but your point of view is. If your story’s bland, the tech just scales blandness.In this episode, Julien Palliere, AI Strategist at Column Five joins Jason and Josh to deliver a necessary reality check.We unpack why “just add AI” is a lazy brief, how

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48:22

Building a Growth Engine That Converts with Nicole...

Best Story Wins ·

2025/10/23

Marketers are hooked on attribution perfection. Meanwhile, your buyers are ghosting and your “AI-powered” campaigns sound like everyone else’s. What if the edge isn’t more dashboards but it’s better judgment?In this episode, Nicole Gates, VP Growth Marketing at Varonis tears up the playbook B2B keeps clinging to. She shows how a “process person” builds a launch machine that actually ships, why tiering by customer impact (not internal hype) changes everything, and how moving SDRs under marketing with

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24:56

The Missing Ingredient to your B2B Strategy with Jess...

Best Story Wins ·

2025/10/16

When everyone’s chasing quick wins, it’s easy to forget the one lever that compounds everything: brand clarity. But cramming “agentic AI” into your homepage won’t save you, it just makes you sound like the chorus.In this episode, we sit down with Jess Ellis, Head of Brand, Content, Creative & Comms at Attentive, to talk about what it really takes to build a brand that drives pipeline in a crowded B2B market. Jess gets candid about bringing a hypergrowth org back to its foundation-mission,

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43:15

The Truth About Category Creation — and Why Most Get...

Best Story Wins ·

2025/10/09

If your marketing feels harder than it should, you’re not imagining it. So what’s the smarter way forward?In this episode, Adam Greco, Product Evangelist at Hightouch argues for a simpler model: composable CDP. Instead of locking yourself into a monolithic suite, you keep data where it already lives and activate it directly. That means days instead of quarters to get value, and less money wasted on campaigns that annoy customers instead of delighting them. Adam pulls from decades in analytics to

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47:36

Community as a Growth Engine with Sandy Mangat of Pocus

Best Story Wins ·

2025/10/02

Everyone’s talking about AI, but let’s be honest, most B2B brands still sound like copy-paste corporate speak. The scary part? While you’re stuck writing “safe” content, your competitors are out there building cult followings.On this episode, Jason and Josh talk with Sandy Mangat, Head of Marketing at Pocus, about what it really takes to make people care. Sandy has worked in product, growth, and brand teams, so she’s here to share the lessons you won’t find in a playbook. From building a community

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49:45

From ABM to Contact-Based Marketing: Jess Cook on...

Best Story Wins ·

2025/09/25

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

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45:55

How Brave Work Actually Gets Approved

Best Story Wins ·

2025/09/18

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,

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53:39

What it Takes to Build a Winning Brand

Best Story Wins ·

2025/09/11

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

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45:10

How to Turn Customers Into Your Loudest Advocates

Best Story Wins ·

2025/09/04

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

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42:46

The Marketer’s Guide to Modern Storytelling

Best Story Wins ·

2025/08/28

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

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43:25

Building a Brand Like a TV Show

Best Story Wins ·

2025/08/21

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,

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54:34

From Forgettable to Unstoppable Brand Moves

Best Story Wins ·

2025/08/14

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

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109 results

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