Dana Walsh leads integrated marketing for Square’s food and beverage business unit within Block, a global technology company focused on economic empowerment and financial access.
For Walsh, the work is personal. As a native New Yorker, food is family, culture, and community, which makes every campaign feel closely connected to the people and businesses Square serves. A self-described full-stack marketer, Walsh views herself as a brief writer, media planner, creative concepting partner, and brand strategist. But what sets her work apart is her understanding of not just what resonates, but why.
That mix of strategic range and human insight is also shaped by her background as a competitive runner. Walsh brings that same discipline to marketing, with a mindset rooted in bold thinking, relentless execution, and measurable impact.
Named to our Marketers to Watch list, Walsh shared her thoughts on AI adoption, the power of human-led creativity, and why the future of brand marketing still depends on real-world connection.
How are you and your team currently using AI?
Block is ahead on AI adoption, and I’ve leaned into it fully. I live in Goose, an open-source AI agent built by Block that I’d recommend to any marketer. I use it to turn seller insights, interviews, and product GTM work into briefs, query dashboards in natural language, automate reporting, optimize media, and synthetic-test creative before launch. But I have a rule right now, one I’d like to follow for as long as possible: AI supports the execution and efficiency, not the creative strategy or vision. I deliberately do the opposite of whatever AI suggests creatively. Bold, culture-driven ideas require human intuition and taste. AI makes me faster and sharper, but the creative vision stays unapologetically human-led.
What’s a prediction you have for marketing over the next few years?
There’s a duality right now: AI is advancing faster than ever, yet people are craving nostalgia, community, and real human connection more than ever. The future of brand marketing is the marriage of both. Smart brands will use AI for scale, targeting, and speed, then invest in unforgettable real-world moments rooted in that longing. We proved this at Square with The Corner Store, a pop-up in San Francisco’s Mission District where our digital brand campaign came to life as a neighborhood gathering space for local businesses. My take is that brands that only show up in feeds will lose to brands that show up in culture.
What’s the most innovative or exciting project you’ve worked on recently?
I created “Only the Good Stuff,” a gated video series that positions Square as the trusted, purpose-built point of sale for restaurants. We partnered with Kelis, the Grammy-nominated artist behind “Milkshake” who is also a trained chef and genuine food-and-beverage insider, as our talent to connect with net new audiences, while our featured sellers reinforced credibility with the upmarket operators already in our ecosystem. What I love most about this project is that the campaign and creative strategy built the entire funnel. One story, one shot, pulled through every channel and stage: awareness through paid and social to reach new audiences, consideration through editorial and nurture to deepen trust, and conversion through sales enablement to close. That’s what excites me: building creativity that doesn’t just live at one stage but works harder across the full journey.
What leadership muscle is most important for marketers to exercise?
Empathy. Not as a buzzword, but as a discipline. As an integrated marketing lead, my job is to connect every channel, every touchpoint, and every message into one cohesive story, but it’s also to connect every team. I sit across the entire organization: brand, product marketing, sales, creative, media. Empathy is what allows me to understand each team’s priorities and translate them into one unified narrative. But it also extends outward. I talk to Block/Square sellers daily, stay embedded in their world, and lead by listening first. The best marketing makes people feel seen, and that starts with making the people around you feel seen too.
What’s the most game-changing piece of career advice you’ve ever received?
I’m a huge fan of Scott Galloway and his philosophy on resilience. Early in my career, I received criticism that made it clear I wasn’t going to be the most knowledgeable person in the room anytime soon. But I could be the most prepared and the hungriest to learn. I believe that education doesn’t end in a classroom. You can create your own degree at any company based on what you want to master. Being open to feedback and criticism, and not taking it negatively or personally, is what makes you grow even more.
What gives you energy and inspiration outside of work?
I live by two mottos: health is wealth and family over everything. Movement keeps me grounded, whether that’s running, surfing, or snowboarding. When I’m not on screens, you’ll find me outside in nature, ideally with family – chasing my nearly 2-year-old daughter. Those moments recharge everything: my creativity, my perspective, and my energy for the work.
Marketers to Watch is a recognition series to spotlight highly innovative and forward-thinking marketing leaders in the community. If you have someone you’d like to nominate for the series, apply here.
