

Best Story Wins
Column Five
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.
Episodes
Mentioned books

Mar 20, 2025 • 40min
The Future of B2B Content Is Video-First with Laura Wilkinson of Vidyard
In today’s world, attention spans are shorter than ever. With this in mind, marketers need to let go of outdated content tactics to embrace the future of B2B content, and some of the best ways to do this is through the smart use of video and leveraging original insights.In our latest episode of Best Story Wins, we sat down with Laura Wilkinson, Director of Brand Marketing at Vidyard, to talk about how video is the not-so-secret weapon for cutting through the noise, and what it means to optimize for content quality over quantity. Laura shares why her team has moved away from the traditional blog, the power of AI avatars in sales, and how great storytelling is the key to building better customer relationships.We also discuss:Why video-first brands are leaving traditional content in the dust.The marketing myths that need to die immediately.How to make your brand unforgettable (without annoying your audience).And much, much more.

Mar 13, 2025 • 34min
Why Brand Awareness Is the New Revenue Driver with Jenny Thai of Vanta
Most B2B content today feels generic: AI-generated fluff, generic SEO blog posts, and bland corporate jargon no one reads. Meanwhile, the brands that stand out—the ones people want to engage with—are playing a different game. So what’s their secret?In this episode, we sit down with Jenny Thai, Head of Content at Vanta, to dig into how to build a winning brand through content. Drawing from her experience in crafting compelling brand narratives, leading content teams, and leveraging expert-driven content, Jenny unpacks how to create content that captures attention, resonates with people, and drives demand. We’re diving deep into:What it takes to evolve a content strategy to move up-market.Why brand awareness drives revenue.What’s legit in AI-generated content, what’s overblown, and how to use it without losing your brand’s soul.The rising power of expert-led content—and why if you’re not embracing it, you’re already behind.And much more.

Mar 6, 2025 • 48min
How AI Is Redefining B2B Marketing Forever with Stewart Hillhouse of storyarb
The marketers who know how to wield AI as a force multiplier are already outpacing everyone else. Are you evolving fast enough to stay relevant?In this episode, we sit down with Stewart Hillhouse, VP of Content at storyarb, to explore the evolving B2B marketing flywheel—where AI, creativity, and strategy must work together to keep brands growing. Stewart explains why the old approach to content marketing is dying and how today’s marketers need to think and work differently in this new AI-powered future.We also discuss:The three high-value roles marketers should be focusing on in 2025.How to build AI-driven workflows without losing the human touch.Why brand trust beats attribution—and what that means for demand gen.The death of massive marketing teams and how to future-proof your career.And much more.

Feb 27, 2025 • 42min
How to Build Brands That Actually Stand Out with Ross Crooks of Column Five
Every brand creates content, but only a few stand out. AI has made it easier for everyone to produce high-quality content, yet most brands get stuck in a cycle where they're creating good enough content but fail to stand out. What does it actually take to break through?In this episode, we interviewed Ross Crooks of Column Five to explain why the past decade's content playbook is dead.Ross shares why brands that aren't differentiated waste their time and resources, and why you should stop churning out content for content's sake and start creating with intent. We also explore:The biggest mistake brands make when trying to stand out (and how to fix it).How to inject real emotion in B2B content.The importance of using AI as a tool for leverage, not a crutch.How thoughtless scaling leads to generic, ineffective content.And much more.

Feb 20, 2025 • 35min
How Mews Builds Emotion Into Every Brand Move with Michael Fitzsimmons of Mews
It can be easy to lose sight of the need for deep emotional connections in a world where everyone seems obsessed with AI, automation, and bottom-funnel conversions. But being able to connect authentically with your customers is the lifeline of every business. In this episode, we sat down with Michael Fitzsimmons, VP of Growth at Mews, who shared how forward-thinking brands reject generic tactics and double down on storytelling, bold positioning, and strategic risk-taking – all with a mind to never rest on one's laurels, but rather to keep setting the bar higher and higher when it comes to quality, connection, and well, growth. He shares how AI fits into the creative process without killing originality, why content needs more taste, and how modern brands must prioritize community-building to stay relevant.We also discuss:Why most B2B brands fail at differentiation—and how to fix it.The importance of owning a category instead of competing in one.Why taste and human creativity are still some of marketing’s biggest competitive advantages.Where AI shouldn’t be used in content marketingAnd much more.

Feb 13, 2025 • 47min
The Secret to Un-Ghosting Prospects with Matt Hogan of HG Insights
The biggest challenge in B2B marketing isn’t so much generating demand, but it’s keeping folks from ghosting you, even long before they enter your pipeline.In this episode, Matt Hogan, VP of Marketing at HG Insights, reveals why B2B buying behavior has radically changed, and how most companies struggle to keep up. He breaks down the rise of shadow buying, the increasing role of CFOs and CIOs in decision-making, and why your brand is being judged before you ever get on a call. We also discuss: Why poor positioning is sabotaging your marketing efforts before they even begin.The new golden age of cold calling.Why generative AI is changing the content game—but most brands are using it wrong.How to leverage data to create magnetic, high-impact marketing.And much more.

Feb 6, 2025 • 35min
How to Stand Out From the 85% with Egan Montgomery of Backstroke
About 85% of competing software companies are pretty much the same.The winning companies focus on staying in the 15% that represents an opportunity to truly differentiate, which is also what the company’s goals should be tied to.In this episode, Egan Montgomery, Co-founder and VP of Marketing at Backstroke, reveals how his generative AI-powered platform is changing how email marketing works, boosting performance by 30% compared to human-written emails. Egan also shares why “doing things that don’t scale” is the future of marketing, and how tailored in-person experiences are becoming the best way to build trust with clients. We also dive into:Why the old B2B marketing models are crumbling and what’s replacing them.How personal branding is no longer optional for founders and executives.Why generative AI’s second wave will change how we work, sell, and connect.Building trust in a world saturated with noise and gimmicks.And much more.

Jan 30, 2025 • 49min
How to Build a Billion-Dollar Brand Through Story with Obaid Durrani of Clay
Your biggest competitive advantage in B2B isn't your product; it's the story that people tell themselves about your company. Today's winning brands shape the story by balancing giving people the content they want while never resting on their laurels. In this episode, Obaid Durrani, of Clay, shares his vision for what this means and gives examples of how he's pushing boundaries and reimagining what b2b content can and should be, which is helping to drive Clay's rapid growth and recent ascension to unicorn status. We also explore:How to turn dry product features into captivating narratives.The formula behind Clay's viral Matrix-inspired campaign.What most brand leaders are still getting wrong about influencer marketing.Why building "conceptual content" is the future of B2B marketing.And much more.

Jan 23, 2025 • 38min
How to Cut Through Digital Noise with Andrew Gori of Autodesk
It’s smart, it’s fun, and it might just change how you think about content. In today’s noisy digital world, Autodesk knows how to stand out: by telling stories that truly matter.In this episode, Andrew Gori takes us behind the scenes of Autodesk’s human-centric content strategy, showing how his team connects with audiences in the construction industry. From his journey as an aspiring journalist to leading bold content strategies at Autodesk, Andrew shares how creativity and strategy come together to rise above the digital noise.We also discuss: AI's impact on content discoverability, the challenges of AI-driven search results, and ongoing strategy experiments.Adapting marketing strategies to become a top content destination and build a loyal audience of "1000 true fans."Autodesk's upcoming global research project revealing groundbreaking insights into the construction industry.

Jan 16, 2025 • 39min
The Power of Creative Restraint with Nate Skinner of Squarespace
The more you post, the less your audience cares. With brands trapped in an endless cycle of content production, is the key to standing out doing less?In this episode, Nate Skinner, Head of Brand Creative Strategy at Squarespace, shares his insights on breaking free from the "always-on" trap. He explores how Squarespace integrates bold creativity with meaningful storytelling, why personal branding is changing the B2B industry, and how AI and curated design are paving the way for successful marketing. We also explore:The shift from quantity to quality in brand storytelling.Why Super Bowl ads are still the ultimate creative risk—and reward.How Squarespace is redefining social media strategy with creativity and focus.The role of AI in crafting high-impact campaigns.How personal branding intersects with corporate identity to drive trust.


