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 level.
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 actu...
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 choi...
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...
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...
Most 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: mediocre work at scale. So what’s actually happening here… is AI making you better, or just faster at being average?
In this episode, Josh sits down with Julien Palliere, Business Development Lead at Column Five to unpack how we cut through the hype and get real about how AI is changing B2B—from strategy and content to client trust and sales. Josh and Julien break down why “what AI says about...
The 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 this episode, Jacqui Morgan, breaks down why most content gets ignored and what it really takes to earn attention, build trust, and drive results. We get into why social is a business driver (not a support channel), why chasing the algorithm is a losing game, and how to shift from “posting to exist” to creating content people actually want. From B2B influencers to employee advocacy, this is a no-BS pl...
AI 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 Global Content Marketing at Varonis breaks down what happens when search stops being clicks and starts being answers. We talk about why the old SEO playbook is getting cooked by AI discovery (AEO/“AI search”), and how B2B teams need to shift from “more content” to more credibility—the kind that gets quoted, sourced, and repeated by LLMs.
We also explore:
Why “being the right answer” beats “being #1” in an AI-first world...
How 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 delivers the reality check B2B teams don’t want—but need: the AI wave isn’t just changing how software gets built, it’s changing where money goes. And if you’re still running marketing like it’s an infinite-seat-count world, you’re basically trying to win Formula 1 with a tricycle.
AI spend is ballooning, everything else is fighting for scraps, and the CMO job is mutating from campa...
The 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 episode, Devin Bramhall, Fractional Chief Growth Officer delivers the uncomfortable truth most teams avoid: B2B companies don’t fail because marketing “needs to do more.” They fail because the funding model doesn’t fit the moment… and the math doesn’t math. And when budgets tighten, the classic response (more content, more tools, more “motions”) isn’t leadership — it’s denial with a weekly standup.
We unpack the real shift happeni...
The 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 episode, Matt Hemsley, Marketing Operations Team Lead at Asana delivers the unsexy truth: the funnel isn’t “broken”—it’s been replaced. He breaks down what happens when AI becomes the new front door, web traffic gets weird, and attribution starts lying to your leadership team with a straight face.
We get into the real power shift happening inside modern B2B orgs: marketing ops moving from order-taker to architect, b...
The 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. If your content still assumes attention is linear, you’re not behind—you’re irrelevant.In this episode, Amanda Verdino, Director of Content Marketing at Forma dismantles the comfortable lies B2B marketers tell themselves about storytelling. We talk about why differentiation without defensible substance collapses under AI scrutiny, how first-party data becomes your only real narrative advantage, and why most “thought leadership” is just recycled opinion dressed up as confidence. Amanda...
How 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 it’s 2019, you’re already invisible.
In this episode, Kyle Denhoff, Sr Director of Marketing at HubSpot, pulls the curtain back on what happens after the inbound era. We get brutally honest about why channel-first thinking is dead, how HubSpot rebuilt itself as a media company inside a SaaS giant, and why “always-on” isn’t a buzzword—it’s survival. Kyle also breaks down how AI is actually being used behind the scenes (no...
The 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 committees and AI-driven discovery, your “best case study” might be your biggest liability.In this episode, Jillian Hoefer (Head of Content at UserEvidence) delivers the reality check B2B teams keep dodging: buyers don’t need more claims—they need credible, searchable, situation-matched evidence that makes choosing you feel safe. Jillian breaks down why the classic “one giant ROI story for everyone” approach erodes trust, how AI search punishes gated proof, and why the winners in 2026 wi...
How 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. In a world where buyers ask ChatGPT first, the homepage isn’t your front door anymore. The chat box is.
In this episode, Kevin White (Head of Marketing at Scrunch) delivers a much-needed reality check on AI Search: there are no true “experts” yet, the platforms are a black box, and anyone selling guaranteed hacks is basically selling essential oils for your funnel.
We also explore:
The one metric that matters first...
AI 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, “more” doesn’t win. Better wins.
In this episode, Jessica Rosenberg (Head of Brand at AirOps) delivers the reality check B2B teams keep dodging: AI doesn’t make marketing magically faster—it makes mediocre faster. Jessica unpacks why AI search raises the stakes on quality, how “AI-first” brands build movements (not feature piles), and why the new moat isn’t content volume—it’s taste, narrative, and systems that actually improve...
AI 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 lays out the uncomfortable new reality: AI assistants are becoming the first stop in the buyer journey—and they don’t “browse.” They decide. Artem breaks down what it really takes to show up inside high-intent AI conversations (and why most brands are accidentally training the models to ignore them).
We also explore:
The 3 pillars of AI visibility: coverage, structure, authority—and how they map to modern content strategyWhy AI ans...
Taste 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 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 healthcare company—thinks about ambient clinical intelligence and why t...
How 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 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 takes to keep quality high when the org is moving at...
The 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 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 stakes, and how human stories, conviction, and point of view become the only defensi...
SEO, 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 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 punish AI-slop; how to merge SEO, AEO, and content into one motion in...
Ditching 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 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, why the CEO (not marketing) owns the brand, and how psychological safety unlocks the kin...
Tomato 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 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 will either thank you or feel attacked.
We also cover:Annual planning as a pow...
The 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 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 unreasonable hospitality to make products and events feel theirs, not “yours.”
We also cover:AEO i...
Everything’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 “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, why “brand” is a budget-killing word (start saying “repu...
Story 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 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 AEO is quietly disintermediatin...
Building 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 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 real SLAs turns MQL theater into pipeline. We dig into the noisy AI arms race (robots fighting robot...
The 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 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, values, and a point of view people can actually feel. We dig into c...
The 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 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 show how organizations can finally stop tripping over their own tech, build trust between data...
Community 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 “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 people actually want to be part of, to cutting throug...
From 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 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 repurposing can multiply your reach, and why even unexpected moments (like a CEO going rogue on LinkedIn) can become...
How 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 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, and how the next wave favors curators who know wha...
How 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, 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 launch a new brand inside a legacy company, how “bo...
Building 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 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 care, how to create a brand th...
The 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 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 how we approach it.
We also discuss:
Why founder co...
How 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 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, shares the real (and often hilarious) sto...
Bold 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 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 it safe, this one’s...
Building 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 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 Faire...
Building 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 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 personality, culture, and staying power into your B2B...
The 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, 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 structure that lets the brand promise echo from awareness to advocacy. It’s not theory—it’...
How 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 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 platform—and why that required more than just a new logo.
We also...
