Why Customer Obsession and AI Make the Strongest Marketing Team

What happens when cutting-edge marketing meets the everyday realities of small business owners? In this episode of Future of Marketing, hosts Mada Seghete and Camille Ricketts talk with Lindsey Irvine, Chief Marketing Officer at Square, about how marketing is fundamentally shifting in an AI-driven world, especially when your audience isn't made up of tech insiders, but real-world business operators. Lindsey brings a unique perspective shaped by her experience across Salesforce, MuleSoft, Benchling, and now Square. At the core of her approach is a relentless focus on customer obsession—meeting business owners where they are, understanding their real-world challenges, and building marketing strategies that prioritize simplicity, trust, and time savings over technical complexity. A central theme throughout the conversation is the emergence of marketing's new "dual mandate." It's no longer enough to create content that resonates with human buyers—you also need to create content that AI agents can discover, interpret, and recommend. As search behavior shifts toward LLMs and AI-powered overviews, traditional SEO strategies are breaking down. Lindsey shares how her team is adapting by prioritizing earned media, community-driven platforms like Reddit and YouTube, and structured, content that signals credibility to both humans and machines. The episode also dives into the operational side of AI in marketing. Lindsey emphasizes that AI is not a shortcut for strategy—it's a multiplier. The real opportunity lies in identifying high-impact workflows that can be automated end-to-end, such as ad bidding, lead scoring, and campaign optimization, rather than simply layering AI on top of existing processes. At the same time, she highlights the importance of maintaining a strong core message that anchors the entire organization, preventing fragmentation across channels, segments, and geographies. Looking ahead, Lindsey believes the future marketing organization will be defined by AI-first thinking, fewer but more empowered teams, and leaders who act as cross-functional "quarterbacks," orchestrating both human and AI resources to scale impact. The mindset is shifting from hiring more people to building systems and even AI agents that can 10x output without increasing headcount.