Out-of-Home advertising has spent the last several years facing the same question being asked across the media industry:

Can you prove it works?

As marketers demanded greater accountability from every channel, the expectations placed on OOH began to change. Reach and awareness still mattered, but advertisers increasingly wanted stronger visibility into how media investments contributed to business outcomes.

When David Krupp became Global CEO of billups in 2018, he saw that shift as an opportunity.

Rather than viewing accountability as a challenge to the industry, billups embraced the idea that OOH could become more measurable, more data-informed, and more connected to the broader media ecosystem without losing the creativity and cultural relevance that have always made the channel valuable.

Today, that leadership has been recognized on one of the industry's biggest stages.

David Krupp has been named the winner of Digiday's inaugural CEO of the Year award at the 2026 Digiday Media Buying & Planning Awards.

The recognition comes alongside another major honor for the company itself: billups was named Most Innovative Independent Media Agency. Together, the awards recognize both the leadership and innovation helping shape the future of Out-of-Home advertising.

Seeing Opportunity Where Others Saw Uncertainty

The media landscape looked very different when Krupp joined billups in 2018.

Advertisers were under growing pressure to justify spending, performance marketing was influencing more media decisions, and expectations around measurement were rising across the industry.

billups believed OOH needed to evolve alongside those changes.

That belief led to investments in technology, audience intelligence, automation, and measurement capabilities designed to help advertisers better understand campaign performance and make more informed decisions.

Underlying those investments was a simple idea:

OOH should be held to the same accountability standards as every other media channel.

At the time, that perspective challenged some long-standing assumptions about the role of Out-of-Home advertising. Today, it aligns closely with what many marketers expect from their media partners.

Under Krupp's leadership, billups expanded into more than 20 countries while continuing to invest in the tools, talent, and expertise needed to support advertisers in an increasingly complex media environment.

Those decisions helped establish billups as one of the companies helping lead the industry's shift toward more measurable and performance-driven OOH.

Recognition Beyond Digiday

The Digiday honors were not the only recognition highlighting billups' leadership this year.

While we didn't take home the award, we're proud to see David Krupp recognized as a finalist for Creative Leader at Campaign's Global Agency of the Year Awards.

The awards celebrate some of the most innovative and influential agencies and leaders from around the world, with entries spanning 85 companies across 16 countries and judged by a panel of senior global marketers.

Being shortlisted reflects David's commitment to challenging convention, embracing new ideas, and helping shape the future of Out-of-Home media during a period of significant change across the industry.

Together, the Digiday and Campaign recognitions point to a consistent theme: leadership that embraces change, questions assumptions, and remains focused on helping clients navigate an evolving media landscape.

Looking Ahead

The future of OOH will be shaped by many of the same forces transforming the broader media industry: automation, AI, improved measurement, and increasingly sophisticated ways of understanding audience behavior.

As those capabilities continue to evolve, advertisers will expect even greater accountability from every channel in their media mix.

David Krupp's recognition as Digiday's 2026 CEO of the Year reflects a leadership approach built around meeting those expectations and helping clients adapt to what's next.

For billups, the awards are a meaningful milestone. More importantly, they reflect a belief that Out-of-Home advertising can continue to evolve while remaining one of the most powerful ways for brands to connect with people in the real world.

As the industry moves forward, billups remains focused on helping advertisers better understand, measure, and maximize the impact of OOH.

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