Creativity is one of the most powerful assets a brand can invest in. But too often, it gets buried under data, deadlines, or disconnected strategy. In Episode 11 of Beyond the Billboard, Charlie Riley sat down with creative leader Dmitry Shamis to discuss how to bring creativity back into focus, especially in the world of out-of-home (OOH) advertising.
Shamis, former global head of creative and brand at HubSpot, recently launched his own agency, oSnap, with the goal of building better brand systems. In this episode, he shared practical advice on blending creativity with structure, leveraging AI without losing your voice, and making OOH media work harder by designing with context in mind.
Watch the full episode below.
Why Creative Leaders Are Rebuilding the Brand Process
Dmitry’s decision to launch oSnap came from years of watching brands struggle after the initial branding work was complete.
“You’ll end up with a PDF and questions on how to leverage it,” he said. That experience is what shaped oSnap’s mission—to give teams not just a brand identity, but a complete system they can actually use.
“Creative should not be a bottleneck. Brand should not be a bottleneck. It should enable every employee, every team to do their best work as fast as possible, go to market, and learn.”
At oSnap, the goal is to empower teams across functions to use the brand in real time, with assets that are flexible, consistent, and built for speed.
The Shift from Digital-Only Thinking to Contextual Marketing
OOH advertising challenges creative teams to think differently. Unlike digital, OOH lives in the real world. It’s physical. It’s public. And it often has seconds, not minutes, to grab attention.
“You must know who’s going to see your ad, where they are, and what state they’re in when they see it.”
That means your billboard can’t be a blog post, and your transit ad shouldn’t try to tell a full brand story. Dmitry explained that success in OOH starts with knowing the context—what the viewer is doing, where they’re going, and what kind of message will make them pause or think.
It’s a reminder that creativity isn’t just about visuals or copy—it’s about placement, tone, and timing.
Building Systems That Support Creativity
Most brands treat creativity as a luxury. oSnap believes it should be a requirement. The agency helps brands set up systems that remove creative blockers, so teams can go to market faster and iterate more confidently.
“We really needed to stop and think about how to build a system that works for as many people as possible while also leaving the door open for us to continue being creative.”
That balance between consistency and flexibility allows creativity to scale. Without it, every creative task becomes a reinvention. With it, teams can build on a strong foundation.
How AI Can Support Creative Work (Without Taking It Over)
AI came up in the conversation as well. Dmitry was clear: AI is not a creative replacement, but it can be a creative accelerator.
“AI is creativity’s best friend. It helps you get out of the busy work.”
Think of AI as a tool for clearing the runway. It can help write drafts, organize thoughts, or test variations. But the real creative spark still has to come from a human.
“It can’t be the brain. You’re the brain. If we don’t come up with it, AI won’t. Whatever it comes up with is just a weird combination of a million different things everyone else has already come up with.”
Used well, AI creates more time for creativity, not less.
Final Thoughts: Bring Creativity Closer to Execution
If your creative work feels disconnected from your media strategy, or if your team is always waiting on the brand team before launching anything new, this episode is a must-listen.
Dmitry’s perspective is simple but powerful: creativity should be foundational, not reactive. It should be embedded in how your brand operates, not just how it looks.
And when it comes to OOH, the opportunity is wide open for teams willing to rethink how creativity manifests in the real world.
Listen to the Full Episode
🎧 Beyond the Billboard Ep. 11: Unlocking Creativity with Dmitry Shamis