What DeeperDive Is and Why It Matters for AI Monetisation
Taboola’s DeeperDive is an AI monetisation platform that turns conversational responses to user queries into new, context-aware advertising inventory for publishers and generative AI companies. Built as a generative AI answer engine inside major publisher sites, DeeperDive converts trusted editorial content into an interactive Q&A experience where readers can keep asking follow-up questions instead of clicking through static pages. The key shift is that this conversational layer now doubles as an ad surface: DeeperDive inserts high-intent ads directly into the AI answer page, so every query becomes a potential commercial opportunity. Under the hood, the platform combines large language models, retrieval systems and Taboola’s proprietary intent graph to generate tens of millions of AI-powered answers each month for more than seven million users, while NVIDIA accelerated computing keeps inference fast enough to feel natural in a chat-like environment.
Opening the Monetisation Engine to Chatbots and Virtual Assistants
Taboola is now taking the monetisation engine that powers DeeperDive and making it available to other generative AI platforms, including chatbots, virtual assistants and conversational agents. Instead of building their own ad tech stacks, AI companies can plug into Taboola’s existing infrastructure and start turning user questions into ad-supported answers. Realize, Taboola’s performance advertising platform, connects tens of thousands of advertisers to these high-intent moments, matching queries with offers that are likely to convert. For AI builders, this effectively extends the same commercial layer that publishers enjoy to standalone AI apps and services. According to Adam Singolda, CEO of Taboola, “today’s news is about helping build the economic layer of the AI internet,” reflecting a view that conversational interfaces will sit at the centre of how people search, compare and decide what to buy.
How Conversational AI Ads Work Inside an Answer
The core of Taboola’s DeeperDive advertising model is conversational AI ads that appear natively alongside an AI-generated response, rather than as separate banners or pop-ups. When a user asks about buying a home, for example, the same interface can surface a mortgage-related offer or other relevant services next to the explanation of interest rates or down payments. DeeperDive’s intent graph and retrieval systems interpret the user’s question, predict commercial intent and choose high-intent ads that match that context. This setup is designed to keep the conversation coherent while creating a natural bridge to products and services. Because the ads are tied to explicit questions, the format behaves more like sponsored recommendations in a search results page than interruption-based display advertising, but inside a chat-style experience where the AI response and the commercial message are tightly aligned.
From Publisher Tool to AI Monetisation Platform
DeeperDive began as a way for publishers to add conversational functionality to articles and unlock extra ad revenue from readers who prefer chat-like discovery over scrolling long pages. Embedded within news and content sites, it lets users ask follow-up questions and explore angles that might not fit in the original piece, creating more engagement and more chances to serve high-intent ads. Now, the same DeeperDive advertising infrastructure is being repurposed as a standalone AI monetisation platform that any generative AI company can adopt. The expansion marks a strategic shift for Taboola: instead of only supplying ad demand to media outlets, it is extending its reach directly into AI-native experiences where there is no traditional pageview but still strong commercial intent. This blurs the line between search, content discovery and conversational assistants as places where advertising can appear.
Building Sustainable Business Models for AI Platforms
For many AI platforms, the business question has lagged behind the technology: how to fund powerful conversational services when users may resist stacking multiple subscriptions. Taboola positions DeeperDive advertising as a third path, alongside paid plans and usage-based APIs, enabling chatbot ad revenue by monetising the questions themselves. With the monetisation engine opened to external developers, AI companies can integrate conversational AI ads without designing their own auction systems, advertiser relationships or targeting logic. As Singolda notes, consumers “won’t subscribe to every AI service they use,” which creates room for advertising and commerce to subsidise access. If this model scales, the economic layer of conversational AI could start to resemble search advertising—high-intent, query-driven and measurable—while still leaving room for premium, ad-free tiers for users or businesses that prefer subscription-based access.
