David Lee embraces discomfort as a compass. That flutter of unease, the fear of falling flat signals to him that something worth doing is around the corner. “You might fall flat on your face. Something great might happen from this… it will make you a better person,” he once said. This mindset fuels his approach as Chief Creative Officer at Squarespace, where he's led the company’s in-house agency to become the most awarded globally, winning accolades from Ad Age, the Art Directors Club, and the One Club for Creativity. Under his leadership, Squarespace campaigns spotlight real customers and push creative boundaries—from Jeff Bridges’ dreamy Super Bowl presence to immersive, second-screen experiences that challenge advertising norms.
Originally from Montreal, Lee charted his path out early, leveraging a talent for design to land a place at the Rhode Island School of Design. He earned his bachelor’s degree in graphic design and now serves as Co-Chair of the RISD Board. At Squarespace, Lee does far more than oversee visuals, he connects the dots between product design, marketing, and web experience. With a career spanning creative stints at Wieden+Kennedy, TBWA, and AKQA, he brought to Squarespace a holistic, boundary-crossing view of design rooted in storytelling and cultural relevance.
Lee’s appreciation for constraints is another key to his creative leadership. At Squarespace, he organizes tightly-knit teams—UX, template, web, and campaign designers around shared space and shared vision. He credits this structure with keeping the design voice unified and nimble. But when it comes to inspiration, he looks beyond the tech world, citing minimalist art installations in Marfa, Texas as a recent creative jolt. “The environment plays just as important of a role in art as does the subject matter,” he noted. For Lee, building digital tools is about more than function, it’s about creating space for individuality, expression, and long-term ownership on the internet. In a world shifting toward rented digital identities, Lee's work champions building your own house and making it beautiful.