At POSSIBLE 2025, Yahoo CRO Rob Wilk shared the company’s “greatest hits with new tracks” approach to reinvention—and explained why client loyalty, not hype, is the real signal of success.
Yahoo’s been around for three decades. But that doesn’t mean we should mistake staying power for standing still.
At POSSIBLE 2025, AdMonsters sat down with Rob Wilk, Yahoo’s Chief Revenue Officer, to discuss how the company is evolving its ad tech stack, doubling down on performance, and cutting through the buzz around AI with actual results.
Instead of chasing hype, Yahoo is leaning into what works. It all starts with a massive loyal audience, rich first-party data, and a DSP that’s quietly building one of the strongest client retention stories in the business.
▶️ Watch the full interview below, then scroll for highlights from our conversation.
A Greatest Hits Album—with New Tracks and Fresh Tech
When asked whether Yahoo’s 30-year mark signals a reinvention or a comeback, Wilk had a better analogy:
“I would say mostly a greatest hits album with a couple of new tracks.”
He pointed to the scale and loyalty behind Yahoo’s flagship properties—Yahoo Sports, Finance, News, Mail—and the rollout of Yahoo Ads, which launched this year to offer advertisers more direct and flexible engagement options.
“You can work directly with us, take advantage of our first-party data and massive audience, and do things that are more bespoke and integrated.”
AI That Delivers, Not Just Demos
When asked about whether AI fits into the ad world, Wilk shared:
“Companies should be able to clearly articulate exactly how they’re using AI.”
At Yahoo, that means:
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Blueprint, the AI engine powering its DSP, from planning to optimization
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Blueprint IQ, a contextual assistant that helps advertisers navigate the platform (not a chatbot, he emphasized—“that was five years ago”)
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AI summaries and personalization within Yahoo News, thanks to its acquisition of Artifact, the latest venture from Instagram co-founder Kevin Systrom
“These are real-world AI use cases happening today—not just buzzwords.”
The Secret to Renewals: Put Advertisers First
“The advertiser’s results are your North Star. It’s the first thing you think about when you wake up, and the last thing you think about when you go to bed.”
Yahoo’s sales team isn’t just chasing more wallet share. The key is proving value. And the metric that matters?
“Renewal. If an advertiser comes back a second, third, fourth, fifth time… I don’t have to ask if they’re happy. I know they are.”
Wilk says Yahoo’s DSP is seeing “unbelievable” retention rates—very close to 100%.
If You Know, You Know: Yahoo DSP’s Quiet Power
When asked why a buyer should choose Yahoo over other DSPs, Wilk answered:
“If you know, you know.”
He points to:
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Longstanding client loyalty
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Clients going onstage to evangelize the product (unsolicited)
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Strong performance driven by Blueprint AI and Yahoo’s Next-Gen Identity Graph (Next-Gen ID)
“Great data. An incredible sales team. A focus on outcomes. That’s how we win,” he said.
And If He Had to Write a Google Headline?
We had to ask. What would it be if Yahoo’s homepage were still a daily destination and he had to headline Google’s current ad tech drama?
“Let’s see if Google can search its way out of this one.”
Then, after a pause:
“Yahoo is built to last. This is just another day for us.”