Expert Mode: Why Your Next Big Brand Play Might Be on the Street Corner
This article was based on the interview with Lindsey Irvine, Chief Marketing Officer at Square by Greg Kihlström, AI and MarTech keynote speaker for The Agile Brand with Greg Kihlström podcast. Listen to the original episode here:
In the relentless pursuit of growth, the enterprise marketing playbook has become remarkably consistent. We are armed with sophisticated AI models, programmatic advertising platforms, and an ever-expanding arsenal of MarTech solutions designed to optimize every click and impression. The prevailing logic is one of scale, efficiency, and technological superiority. We A/B test our way to incremental gains, build complex attribution models, and speak in a language of acronyms that would mystify anyone outside our operational silos. Yet, for all this optimization, a nagging question persists: in a world saturated with algorithmically-generated content and hyper-targeted ads, are we losing the plot? Are we so focused on the “how” of reaching customers that we’ve forgotten the “why” they should care?
This is the strategic crossroad where many brands find themselves. The temptation is to double down on technology—to shout louder, target more precisely, and automate more aggressively. But what if the most potent strategy isn’t found in a new software stack, but in a fundamentally different approach to communication? Square, a company synonymous with technological disruption in the payments space, is making a compelling case for just that. Under the leadership of CMO Lindsey Irvine, the fintech giant is deliberately pivoting away from a purely feature-focused narrative and investing in a strategy grounded in the authentic voices of its customers. This isn’t a superficial nod to “customer-centricity,” but a comprehensive brand evolution that reasserts relevance by amplifying the very communities it serves. It’s a lesson for every marketing leader grappling with how to build a durable brand in an increasingly ephemeral digital landscape.
The Critical Distinction: From Small Business to Local Business
For any brand strategy to succeed, it must be built on a deep, almost cellular, understanding of its target audience. For years, Square has been the champion of the “small business.” But as Irvine and her team dug deeper, they unearthed a more powerful, emotionally resonant identity that would become the foundation of their new approach. It wasn’t just about size; it was about place.
“We’ve always grown up as being for small business, but as we actually dug in to the breadth of Square customers today, what we actually realized we stood for is not just small business, but local business… what they all have in common is they’re more than just a restaurant or a coffee shop or a salon, they really are part of their local community. And that is a key reason why they started. That is a key factor to their growth. So we really at the center, we’re for the local business, not just the small business.”
This distinction is more than just semantics; it’s a strategic pivot. “Small business” is a functional descriptor based on revenue or employee count. “Local business” is an identity rooted in community, connection, and purpose. By centering their brand on this identity, Square shifted the conversation from what their product does (enables transactions) to who their customers are (community builders). This insight informed their entire “See You in the Neighborhood” campaign, transforming it from a simple tagline into a promise to show up, invest in, and celebrate these local heroes. For enterprise leaders, the lesson here is profound. How well do you truly understand the core identity of your customers beyond their firmographics? Moving from a functional definition to a purpose-driven one can unlock a far more potent and defensible brand narrative.
The Power of the “Local Celebrity”
Once a brand commits to an authentic, community-driven platform, the next challenge is execution. The default for many large brands is to hire well-known celebrities or influencers to lend credibility. While sometimes effective, this approach often carries the faint scent of a transaction—an endorsement for hire. Square chose a different path, recognizing that the most influential voices weren’t on a Hollywood red carpet, but behind the counters of the businesses they serve.
“We’re not using like flashy celebrities that don’t tie to our brand to try and create relevance, right? Like we are literally the center of our campaign, our TV spots, our ads… we’re hering real local businesses who by the way, are celebrities in their own right, in their own neighborhoods. And so it’s kind of a flip of the table of using local heroes, local influencers that are actually the business owners that we all know and love in our own communities and giving them the spotlight to tell their story.”
This strategy does two things brilliantly. First, it ensures unimpeachable authenticity. The stories are real, the passion is genuine, and the connection to the brand is organic. Second, it respects the audience’s intelligence. Customers, especially in the B2B or prosumer space, can spot a scripted testimonial from a mile away. Irvine notes their approach is to go into the business owners’ actual establishments and let them tell their stories unscripted. This surrendering of control is terrifying for many marketers, but it’s precisely what generates the most compelling and trustworthy content. It replaces the polished, corporate-approved veneer with something far more powerful: the gritty, inspiring reality of building a business. The takeaway is clear: your most powerful advocates are likely already on your customer roster. The challenge isn’t finding them, but having the conviction to give them the microphone without a script.
Connecting Brand Investment to Business Outcomes
Of course, a conversation about brand strategy in any boardroom will inevitably—and rightly—turn to measurement. The age-old tension between brand and demand marketing can paralyze even the most innovative teams. How do you justify significant investment in what can feel like a less tangible “vibe” when performance marketers are tracking cost-per-acquisition to the fourth decimal place? Irvine offers a refreshingly clear framework for connecting these seemingly disparate worlds, especially in an era of AI-generated “slop.”
“In a world of AI generated content and AI bots and kind of AI slop everywhere. Brand is the one thing you can’t fake… that is your moat. And without that, you’re one of many… 95% of your buyers… are not in market to buy at any given time. So all of your performance demand dollars are going to the 5% that are ready to click by now. Brand allows you to reach the 95%, create interest, create excitement, create authentic connection, and be in the consideration point when that 95% becomes the 5% ready to buy.”
This is the argument every brand-focused CMO needs to articulate. Brand marketing is not a cost center; it is a long-term pipeline generation engine. By building resonance with the vast majority of the market that isn’t actively buying, you are ensuring that when they are ready, your brand is on their shortlist. Irvine connects this directly to hard metrics, noting that strong brand work should lead to a measurable lift in organic traffic, which is known to convert at a higher rate than paid traffic. She even points out that strong brand investment can increase the efficiency of paid performance spend. This model transforms brand from a nebulous concept into a strategic investment in future revenue, creating a moat that competitors focused solely on bottom-funnel tactics cannot replicate.
The journey Square is on offers a compelling blueprint for any enterprise marketing leader looking to navigate the complexities of the modern market. It’s a strategy built on conviction—the conviction that deeply understanding your customer’s identity is more important than just tracking their behavior, that authentic stories resonate more than polished advertisements, and that building a lasting brand is the most durable competitive advantage of all. It requires a delicate balance of art and science, of qualitative insight and quantitative measurement.
This approach isn’t necessarily easier. It requires more listening than shouting. It demands a willingness to cede control of the narrative to your customers and the courage to defend long-term brand building in a world obsessed with short-term results. But as we move further into an age where technology can replicate tactics with alarming speed, the human element—the genuine connection, the shared purpose, the authentic story—becomes increasingly scarce, and therefore, increasingly valuable. The work Irvine and her team are doing at Square serves as a powerful reminder that sometimes, to cut through the digital noise, you don’t need a bigger amplifier; you just need to get closer to the source.
