Taboola Breaks Boundaries with Microsoft Ad Deal and New AI Ventures

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Introduction: A Bold Move Beyond Native Ads

In a major shift that marks a new era for one of the biggest names in native advertising, Taboola has announced a strategic partnership with Microsoft to handle display ads across several key Microsoft properties. This includes MSN.com, Outlook, and even the broader Office Suite. It’s a clear sign that Taboola is no longer content to stay confined within the native advertising niche it dominated for nearly two decades. With a new platform, fresh innovations in AI, and a growing appetite for market share, Taboola is stepping into territory traditionally ruled by giants like Google and Meta. This expansion also highlights a broader trend in the ad tech world: the race to own first-party data and redefine performance advertising.

Major Strategic Shift:

Taboola has secured a pivotal partnership with Microsoft, giving it the rights to manage and sell display advertisements on platforms such as MSN.com, Outlook, and other parts of Microsoft’s Office ecosystem. This represents a significant departure from Taboola’s traditional focus on native advertising and opens up a new front in its expansion into the display ad market. This move follows Taboola’s recent launch of its Realize platform, designed to support performance ads like vertical videos and social media formats across the open web.

Unlike broad brand-building campaigns, Realize is focused on delivering results-oriented performance advertising. While it will support video content, the emphasis is on social media video rather than high-end connected TV formats. Taboola is leaning heavily on its vast pool of first-party data gathered from over 18,000 advertisers and 9,000 global publishers. This data is a key competitive edge, particularly in a market where companies like Google and Meta have long reigned due to their data dominance.

CEO Adam Singolda believes that Realize offers a real opportunity to chip away at the duopoly’s control of display advertising. This new initiative builds on previous milestones such as Taboola’s 2023 \$1 billion ad deal with Yahoo and its exclusive agreement with Apple to place ads in News and Stocks apps. Taboola also has a long-standing strategic partnership with Microsoft, which was deepened in 2021 with the launch of an open web audience network.

Singolda sees Realize as a valuable tool not only for advertisers but also for publishers, potentially offsetting losses from the declining programmatic ad revenue over recent years. In parallel, Taboola is also launching its AI-powered generative search engine, DeeperDive, targeted at publishing partners like USA Today and The Independent. This signals another layer of innovation as Taboola positions itself at the crossroads of native advertising, AI, and performance media.

These moves are taking place as the advertising industry navigates a climate filled with economic uncertainty and regulatory scrutiny. Concerns over the impact of political developments, especially under potential Trump economic policies, are already pushing some companies to cut forecasts. Still, Taboola is doubling down on growth, confident that its data-driven platform can help publishers thrive in the evolving digital ecosystem.

What Undercode Say: Deep Dive Into Taboola’s Strategic Pivot

Taboola’s bold foray into display advertising is far more than just a business expansion — it’s a strategic recalibration aimed at disrupting entrenched digital advertising models. For years, Google and Meta have held an unshakeable grip on the display ad space due to their massive first-party data resources and algorithmic supremacy. What Taboola is attempting with Realize is nothing short of reclaiming control for the open web by giving publishers and advertisers an alternative fueled by deep, user-centric insights.

The core advantage Taboola wields is its treasure trove of first-party data. In an environment where third-party cookies are fading, first-party data is becoming the new currency. Taboola’s long-standing relationships with thousands of advertisers and publishers give it a unique reservoir of behavioral insights that can be applied to optimize performance-based campaigns. This is precisely the kind of edge needed to effectively compete with platforms like Facebook Ads or Google Display Network.

The focus on social video formats is especially savvy. Rather than trying to replicate the expensive, high-production-value model of connected TV, Taboola is betting on scalable video formats that align with modern scrolling behavior and mobile engagement. Vertical videos that blend seamlessly into social-style feeds can be highly effective at driving conversions, especially for performance advertisers.

Another fascinating component is the launch of DeeperDive, a generative AI search engine customized for publishing partners. This isn’t just a tool — it’s a statement. Taboola wants to help publishers regain autonomy from platforms that have historically monopolized content discovery. By embedding AI search capabilities directly within publisher ecosystems, it helps keep audiences engaged on-site, increasing both dwell time and monetization opportunities.

Taboola’s history of strategic partnerships also supports its ambitious plans. The decade-long collaboration with Microsoft laid the foundation for this latest ad deal, while its agreement with Apple proves its ability to align with tech heavyweights. Moreover, the billion-dollar Yahoo agreement reflects a confidence in long-term performance.

However, risks remain. While first-party data is powerful, Taboola must prove it can rival the user-level targeting precision offered by Meta and Google. Advertisers are notoriously cautious when shifting budget allocations, especially in uncertain economic climates. With digital ad growth slowing, every dollar must yield measurable returns.

Additionally, Realize must demonstrate not just capability but consistency. If campaign performance doesn’t meet advertiser expectations, adoption could falter. Similarly, DeeperDive’s success will depend on seamless integration and real-world effectiveness for publishers.

Nevertheless, Taboola is playing the long game. Its strategy is holistic — spanning performance media, data infrastructure, and AI-enhanced publishing. If executed well, it could not only unlock new revenue for publishers but also shift market dynamics in favor of more distributed ad ecosystems. The company’s moves reflect an understanding of where the web is heading: a fragmented, privacy-conscious, AI-enhanced, and performance-driven landscape.

Fact Checker Results

✅ Is Taboola entering the display ad market? Yes.
✅ Is Taboola using first-party data as a key advantage? Yes.
✅ Has Taboola partnered with Microsoft for ad services? Yes.

Prediction: Where Taboola Is Headed Next

🚀 Expect Taboola to become a serious challenger in the performance advertising sector over the next 2–3 years.
💡 More publishers will likely adopt DeeperDive, especially if it proves effective in boosting engagement and ad revenue.
📈 As economic pressures mount, advertisers may shift a portion of their budgets from traditional platforms to Realize, particularly if it can demonstrate better ROI and deeper audience insights.

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