When we launched the Best Story Wins podcast a little over a year ago, we had a simple mission: Find out how the best brands are winning hearts, minds, and market share through powerful storytelling. After 50+ conversations with some of the brightest minds in marketing and branding, I’ve walked away with insights that have transformed how I think about our work at Column Five, how I think about our clients’ challenges, and more. (It’s amazing how, just when you think you know everything there is to know, one conversation can change everything.)
It’s been refreshing and eye-opening to gain greater perspective beyond Column Five’s four walls, and it’s shown me how similar marketers’ challenges are (regardless of industry). So, after 50+ conversations, I’ve compiled the 10 biggest lessons/takeaways that have stood out to me. I think they can help any marketer improve the way they work and the results they get—and I hope they help you in particular.
1) The doers aren’t always the talkers.
For every marketing influencer with 100K LinkedIn followers, there are dozens of brilliant minds quietly transforming their organizations from the inside. I’ve had the privilege of speaking with marketing leaders who are driving incredible results for their companies but rarely appear on the conference circuit or publish thought leadership pieces. One CMO I spoke with manages a massive marketing budget but had never been on a podcast before. Why? They’re too busy executing.
The takeaway: Not only do I think that more marketers need to build personal brands to share their expertise but I think marketers need to remember there are plenty of people doing amazing work behind their company walls. Those people hold a wealth of untapped wisdom that can be translated into high-value content that your audience can connect with. Whether it’s an article, Q&A, expert panel, or podcast, see our tips to turn your fellow employees into expert content creators.
2) B2B vs. B2C: same strategy, different tactics.
Building brands in B2B and B2C isn’t that different. Regardless of the audience, the core of your strategy is storytelling—specifically, storytelling that makes your audience feel a certain way. This is especially important to remember in B2B. The people who are making buying decisions are still people, and they want to feel engaged and inspired by your brand.
Of course, the difference in B2B is that you’re dealing with a more complex buyer journey, a larger group of individuals, longer timelines, and different channels. But understanding the core elements of your brand story (including your purpose, vision, mission, and values) is crucial if you want to communicate effectively.
For example, Drew Hoffman (VP of Brand at SentinelOne) talked about how they’ve transformed technical cybersecurity content into compelling storytelling by focusing on the “defenders” narrative—positioning their customers as the heroes protecting their organizations. This is a perfect way to engage their audience and invite them into the SentinelOne story.
The takeaway: Whether it’s shaping compelling narratives in your case studies or using creative storytelling to break out of the boring B2B mold, look for every opportunity to reinforce your brand story throughout your buyer journey. (For more on that, see our tips to master brand storytelling.)
3) Good storytelling can come from unexpected places.
Turns out there are a lot of people out there who love to nerd out on the topic of brand if given the opportunity.
I’ve been genuinely surprised by how many leaders—not just in marketing—have a deep passion for brand strategy and storytelling. From CTOs to operations leaders, I’ve gleaned tons of insights on the art and science of brand building. I’ve also been delightfully surprised by where people source their storytelling inspiration from. For example, I enjoyed hearing how Drew Hoffman draws his marketing inspiration from film directors. (Turns out, there’s a lot that marketers can learn from those directing legends.)
The takeaway: Good marketing ideas don’t have to come from the standard playbook. Non-marketers also have fresh perspectives that can do a lot to breathe new life into a stale strategy, so consider looping them into content audits or brainstorms. Staying open to others’ insights and ideas can help you come up with some truly standout content.
4) “Brand” isn’t a trend. It’s a strategy-level decision.
This isn’t opinion; the research backs it up. According to McKinsey, strong brands outperform weak brands by 20% in terms of financial performance. Over and over, I’ve heard guests talk about why investing in your brand is so important—and why it remains integral to their success. (This sentiment also spans industries, from SaaS to sports.)
At Column Five, we’ve been pushing the power of brand for over a decade. But it’s more relevant than ever. In a world of oversaturation and a lack of differentiation, cultivating a unique brand is the only way to maintain your competitive advantage.
The takeaway: If you want to be successful, you need to focus on creating a memorable brand. How do you do that? Ross Yoshida (Senior Director of Graphic Design for the Los Angeles Dodgers) calls it finding your “hot sauce”—the special, unique thing that makes your brand stand out.
5) AI’s role has drastically evolved.
AI is less of an existential threat than it was a year or two ago.
The conversation has already shifted dramatically since we started the podcast. Initially, there was deep concern about AI replacing creative roles. However, now that we’ve seen the flood of subpar AI-generated content, it’s clear that human intervention is still needed to make sure content is accurate and engaging.
The takeaway: AI can generate expertise, but it can’t generate experience. If you want to create truly compelling brand storytelling, infuse content with unique insights, experiences, and perspectives that make it really stand out.
6) AI adoption creates competitive advantage.
A lot of brands have experimented with AI tools. But the gap between teams effectively leveraging AI and those resisting it (or using it ineffectively) is widening rapidly.
The guests who are actively experimenting with tools, building fresh workflows, and—most importantly—sharing those learnings with their larger teams, are the ones who are clearly operating on a different plane. They’re seeing substantial productivity gains in content creation and analytics tasks, improving both their team’s results and their bottom line.
The takeaway: Identify repetitive, low-creativity tasks in your marketing workflow that could benefit from AI tools to free your team to focus on strategic thinking and creative direction. Start with small, measurable projects and scale based on proven results.
7) Organizational structure isn’t consistent—and it doesn’t need to be.
In talking with our guests, I’ve learned that there are a lot of smart ways to set up a creative and/or marketing org that partners with sales and other teams.
Some centralize all creative and marketing functions, while others distribute them throughout the organization. Some place brand and demand generation under one leader, while others separate them entirely.
There is no one-size-fits-all approach or best practice. The right organizational structure depends entirely on your company’s stage, goals, and culture.
The takeaway: Rather than searching for the “perfect” marketing org structure, focus on creating clear processes, communication channels, and accountability regardless of how your team is organized. Evaluate based on outcomes and cross-functional collaboration rather than adhering to a particular structural model.
8) Good content is the foundation of a strong brand.
Despite the proliferation of new channels and technologies, good content is still the bedrock of success for any brand. However, with the proliferation of AI-generated content, good content is increasingly hard to find.
As Nate Skinner (Head of Brand Creative Strategy at Squarespace) pointed out on the podcast: Maintaining quality is increasingly challenging when brands want to pump out 30 assets for every day of the week. If brands want to stand out (especially against AI-generated content), they need to prioritize high-value content that is truly helpful to their audience.
The takeaway: Focus on value and quality over quantity. Essentially, consider making less content—but better.
9) Scaling quality content is never-ending work.
Creating quality content at scale—while continuously shaping your strategy around a changing market—is perhaps the greatest challenge marketing leaders face. You need the right team. You need effective communication. And you need to be hyper aware of how each piece of the content machine affects the other.
For example, as Tamara Austring (Senior Design Producer at Zapier‘s Brand Studio) pointed out, designers dread navigating through long briefs. They need clear and succinct directions to be successful—and it’s a marketer’s job to give that to them if they want to scale effectively.
The takeaway: To build content operations that can scale, you need a clear content infrastructure, defined roles, and the tech stack to support your work. Revisit these processes quarterly to identify bottlenecks and opportunities for improvement.
10) Community building is key.
Whether it’s online or offline (or a mix of both), companies that can build communities that invite people into what they’re building are going to be the most likely to win.
The key, as Lindsey Slaby (founder of Sunday Dinner) emphasized, is building curated communities to build those connections. For example, she built a 400-member Slack group that sparks collaboration and innovation among top-tier marketers and creatives.
The brands that stand out aren’t just broadcasting messages—they’re creating spaces for genuine connection and co-creation with their audiences.
The takeaway: The line between brand and audiences is blurring. Look for opportunities to transform one-way communications into two-way conversations. This could be through dedicated community platforms, events, or even by inviting audience participation in content creation and product development.
My Biggest Takeaway
After 50+ episodes of the Best Story Wins podcast, the common thread across all these lessons is that brand building (and, really, brand storytelling) is becoming increasingly integrated with business strategy. It’s not a separate function—it’s a core driver of business success. If you want to succeed in the next year, the next decade, the next century, strengthening those skills is an absolute imperative. After all, in business as in life, the best story wins.
