Technology The Drum Awards

Judge of the Day: Tom Ajello charts the next era of digital experience

By Margo Waldrop, Content Writer

The Drum

December 4, 2025 | 4 min read

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Lippincott’s global experience lead explains how AI, trust and brand clarity are shaping the future of digital experience.

Tom Ajello has been building at the edge of digital for more than 20 years and this year he brings that perspective to The Drum Awards Festival as a Digital Experience judge. As global director of experience, innovation and engineering at Lippincott, he sees the future starting with intelligence that adapts in real time. He believes AI is pushing digital experience past simple personalization and into something more fluid. “By leveraging AI models to track micro-behaviors and analyze user data, brands can create predictive and adaptive experiences that respond in real time,” he says. He calls this a “dynamic experience layer,” a structure that can assemble moments on the fly and let agentic interfaces act as “personalized front doors,” replacing static navigation with something intuitive and individual.

Creativity still sits at the center for him. “Seamless functionality is now a baseline. It’s table stakes,” he says, but he argues that brands don’t need to choose between flawless usability and memorable character. AI gives them room to be “brilliant, brief and strategic,” showing up with emotional precision without sacrificing ease. That lens also shapes how he thinks about unifying mobile, web and in-store interactions. “Unification isn’t about perfect technical consistency. It’s about deepening brand connection and emotional resonance,” he says, noting that chasing efficiency for its own sake often leads to overengineering that dilutes the brand’s voice instead of strengthening it.

Ajello also warns that the most overlooked part of digital experience is trust. As he puts it: “In the new AI-shaped web, AI doesn’t judge brands emotionally. It audits them based on proof points.” Every post, touchpoint and interaction becomes a receipt that signals authenticity. “Trust isn’t a system. It’s a message,” he says, and the brands that communicate it clearly will be the ones AI elevates, not ignores. Looking at what teams need next, he believes the critical skill is learning how to amplify human judgment with machine intelligence. “AI will not replace the need for human oversight. It will empower teams to turn their expertise up to eleven.”

Right now, his biggest challenge is helping clients move away from a narrow efficiency mindset and toward something he calls BX: brand experience. “The goal is to focus on high-priority moments that truly matter,” he says, using brand strength to shape interactions instead of shaving off microseconds. And when asked where he’d invest in 2025, he rejects the idea of picking a channel at all. “The traditional concept of a single channel is becoming obsolete,” he says. People move through a flow of touchpoints now, and the brands that design for that ecosystem, not a linear path, will define the next phase of digital experience.

Be part of what is next at The Drum Awards

The Drum Awards Festival celebrates the leaders shaping digital experience in a year defined by AI, trust and rapid innovation. Follow jurors like Tom Ajello as they set the standard for what meaningful digital work looks like in 2025.

Technology The Drum Awards

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Lippincott

Lippincott is a global brand, marketing and experience consultancy committed to helping companies address their most complex brand challenges. Identifying fresh...

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