Shows / Best Story Wins
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…
Episodes
Best Story WinsYour Buyers Decided Before They Met You with Cristina Bravo Olmo from ThoughSpot
Your buyer has read the reviews, polled their peers, and asked ChatGPT to rank your category. You only found out when they showed up with a shortlist, if you…
Best Story WinsBuild a Personality Before an Agent Picks Your Competitor with Dave Breckon of Carta
Your CFO just found out AI agents can do the buying, and now they want to know why you still need a creative team. If the brand's only job is getting picked by…
Best Story WinsMomentum Beats a Big Launch, Every Single Time with Nick Farrar of Shaped By
A CEO shows up ten minutes late to his own rebrand kickoff, announces he doesn't have time for it, and hands the whole thing to a marketing manager. Nick…
Best Story WinsB2B Branding Was Never Supposed to Be Boring with Wesley Bancroft of Lunour
Your logo hasn't changed in three years and your brand still feels broken. That's not a design problem, it's everywhere else you stopped paying attention…
Best Story WinsPublishing More Is Making You Less Credible with Ben Hasskamp
You've published four posts a week for a year, and your buyers still can't tell anyone what your company believes. Somewhere in all that output there should be…
Best Story WinsTaste beats Trends with Nick Sickleton
Everyone with a prompt window now calls themselves a creative, and the feed shows it: the same look, the same motion, the same instantly forgettable output on…
Best Story WinsWhy Content Systems are the Future with Ross Crooks of Column Five
Everyone on your team can suddenly make content. That's not the win it sounds like, it's how a brand starts dissolving, one "good enough" post at a time. Ross…
Best Story WinsThe Small Team Advantage: Turning Size into a Superpower, with Maria Irie of Chili Piper
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…
Best Story WinsBeige Is What Happens When Nobody's Brave Enough to Be Wrong with Sonja Silveira of Cisco
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…
Best Story WinsAI Made Brand the Only Thing Left That Matters with Adam Morgan of Twilio
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…
Best Story WinsTaste Is the Only Thing AI Can't Generate (Yet) with Matt Scribner of Atlassian
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…
Best Story WinsStop 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…
Best Story WinsWhy 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…
Best Story WinsThe 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…
Best Story WinsClarity 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…
Best Story WinsThe 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…
Best Story WinsIn 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…
Best Story WinsThe 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…
Best Story WinsThe 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…
Best Story WinsStop 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…
Best Story WinsThe 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…
Best Story WinsMost AI Advice Is Completely Wrong with Julien Palliere from Column Five
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…
Best Story WinsThe Content Mistake Killing Your Growth with Jacqui Morgan
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…
Best Story WinsAI Just Changed Content Marketing Forever with Lexi Croisdale from Varonis
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…
Best Story WinsHow AI is forcing CMOs to Adapt and Evolve with Julien Sauvage from Cordial
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…
Best Story WinsThe Sea Of Sameness Is Your Opportunity with Devin Bramhall
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…
Best Story WinsThe Funnel Is Dead And Your Team Hasn’t Noticed with Matt Hemsley from Asana
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…
Best Story WinsThe Real Reason Your POV Isn’t Landing with Amanda Verdino from Forma
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…
Best Story WinsHow Loop Marketing is the Answer to the Death of Inbound with Kyle Denhoff
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…
Best Story WinsThe Only Content That Cuts Through with Jillian Hoefer Head of Content at UserEvidence
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…
Best Story WinsHow to Build a Winning Brand in the Era of AI Search with Kevin White Head of Marketing at Scrunch
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…
Best Story WinsAI Content Volume Won’t Save You with Jessica Rosenberg Head of Brand at AirOps
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…
Best Story WinsAI Visibility Is The Only Way to Win with Artem Kubatkin of Attune
Your SEO traffic isn’t “dipping.” It’s getting mugged in broad daylight by AI Overviews and answer engine output. In this episode, Artem Kubatkin of Attune…
Best Story WinsTaste as a Secret Weapon with Jeff Stark of Suki AI
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…
Best Story WinsHow to Increase Brand ROI Through Scale, Speed, and Quality” with Dan Schwer of Rippling
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…
Best Story WinsThe Bold Bet Smart CMOs Are Making in 2026 with Sylvia LePoidevin
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…
Best Story WinsSEO, AEO, and the Return of Good Marketing with Jenna Hannon of Hatter
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…
Best Story WinsDitching Best Practices: How Courageous Brands Get Remembered with Udi Ledergor of Gong
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…
Best Story WinsTomato Sauce and the Stories Behind What We Buy with Andrew Lee of Microsoft
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…
Best Story WinsThe Feeling of Knowing: Brand in the Age of LLMs, with Ari Yablok of Island
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…
Best Story WinsEverything’s Changing: How Smart CMOs Stay Ahead with Drew Neisser of CMO Huddles
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…
Best Story WinsStory Is the Moat: How to Build One at Scale with Julien Palliere of Column Five
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…
Best Story WinsBuilding a Growth Engine That Converts with Nicole Gates of Varonis
Marketers are hooked on attribution perfection. Meanwhile, your buyers are ghosting and your “AI-powered” campaigns sound like everyone else’s. What if the…
Best Story WinsThe Missing Ingredient to your B2B Strategy with Jess Ellis from Attentive
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…
Best Story WinsThe Truth About Category Creation — and Why Most Get It Wrong with Adam Greco of Hightouch
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…
Best Story WinsCommunity as a Growth Engine with Sandy Mangat of Pocus
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…
Best Story WinsFrom ABM to Contact-Based Marketing and Building a New Category with Jess Cook of Vector
Marketers are under constant pressure to prove impact. Often with smaller teams and tighter budgets. The challenge? Balancing brand building with demand…
Best Story WinsHow Brave Work Actually Gets Approved with Andrew Chen of Hive
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…
Best Story WinsHow to Build Brands That Break the Rules and Win with Scott Smith of Intercom
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…
Best Story WinsBuilding Brands People Actually Care About with Steph Bowker of Metaview
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…
Best Story WinsThe Marketer’s Guide to Modern Storytelling with Roman of Sifflet
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…
Best Story WinsHow to Turn Marketing into Entertainment with Chris Cunningham of ClickUp
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…
Best Story WinsBold Moves That Build Real Brands with Bill Macaitis of SaaS CMO Pro
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…
Best Story WinsBuilding Trust in a Noisy World with Kelly Phillips of Faire
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…
Best Story WinsBuilding B2B Brands with Authentictiy with Kevin Branscum of Typeform
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…
Best Story WinsThe Quiet Revolution Behind B2B Brand Wins with Deanna Adams of Dropbox
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…
Best Story WinsHow to Rebuild a Legacy Brand from the Ground Up with Carla Weis of Docusign
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…
Best Story WinsHow to Build a Brand with Bite with Emily Anne Epstein of Sigma
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 Anne Epstein, the…
Best Story WinsThe Unscalable Stuff That Scales with Ross Mayfield of Zoom
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…
Best Story WinsWhy Trust Is the New Brand Currency with Ethan Bloch of Hiro
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…