Empathy at scale: What Headspace and Dotdash Meredith are teaching us about AI

LAS VEGAS — Picture this: It’s the height of the holiday season. A young mom, juggling work, kids, and chaos sees an ad that doesn’t try to be clever — it simply gets her. It acknowledges her stress, offers empathy, and suggests a mental health tool that might actually help. That ad wasn’t dreamed up late at night by a team of agency creatives. It was built by AI.

That’s what Headspace and Monks achieved in their latest seasonal campaign. Using generative AI tools like Adobe Firefly and proprietary solutions like Monks’ Persona Flow, they created over 460 versions of emotionally resonant ads — tailored to states such as grief, burnout and loneliness. The result? A 62% lift in conversion rates and a 13% drop in cost per signup. It’s proof that AI, when used with care, can do more than scale impressions — it can scale empathy.

That theme echoed across Adexchanger’s Programmatic I/O stage at the Park MGM in Las Vegas. This year’s standout sessions moved beyond the AI hype cycle and instead focused on its impact on tone, intention and connection. Marketers are no longer asking if it should they should use AI anymore. They’re focused on how to use it strategically to create, buy and optimize campaigns.

As ad veteran and self-proclaimed “digital prophet” David Shing — aka Shingy — declared in his keynote speech: “If it can be automated, it will be automated.”

Not just automated, empathically effective

For Headspace, the goal wasn’t more content, it was more empathetic content.

“We’re moving from personalization to relevance,” said Connie Chan Wang, SVP of Marketing at Headspace. “It’s not just knowing your name. It’s understanding your emotional state and offering something that actually helps.”

Monks’ Persona Flow simulated conversations with the brands’ key audience segments — like overwhelmed caregivers and empty nesters — generating nuanced messaging grounded in real consumer insight. These messages were paired with contextually generated visuals via Adobe Firefly to match the emotional tone.

“We fed the algorithms hundreds of creative assets,” said Brittany Blanchard, EVP of Digital Media at Monks. “The more we gave them, the better they got at serving the right message to the right person.”

And what once took weeks? Now done in a third of the time. But the speed is just a bonus.

“It’s about showing people we see them,” said Wang. “That’s what builds trust. That’s what builds brand.”

AI-driven service

For publisher Dotdash Meredith — which owns over 40 titles including Martha Stewart Living and Better Homes & Gardens — AI is being deployed to help readers find exactly what they need with less friction or intrusion.

“We’ve always wanted to help people make better decisions,” said Dr. Joetta Gobell, SVP of Data Strategy and Insights. “AI is helping us finally do that at scale, with nuance.”

Instead of targeting based on identity or third-party cookies, Dotdash Meredith’s Decipher platform uses AI to infer intent based on content behavior. A reader researching family travel might be served relevant content or product suggestions in parenting tech reviews, budget planning content, or road trip recipes — delivered at moments when they’re most helpful. Such suggestions are surfaced contextually across the publisher’s massive editorial footprint.

“We’re not trying to insert ads into content,” said Gobell. “We’re trying to make the ad part of a helpful experience.”

Their partnership with OpenAI enables the team to map intent across the open web — extending their audience signals beyond their owned properties. And it’s not just about where ads show up. Dotdash Meredith is also using AI to personalize how content is delivered, dynamically adjusting information down to the paragraph level based on reader behavior.

In testing, new interactive ad units that respond to the surrounding content in real time drove a 4x increase in engagement and a 20% clickthrough rate to advertiser websites. In other words, less friction, more relevance.