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Tech · 2 min read17 June 2026

Taboola Will Now Sell Ads Inside AI Answers. The Chatbot Is the New Ad Network.

Taboola is opening the monetisation engine behind its DeeperDive answer engine to AI companies, letting chatbots and virtual assistants insert sponsored recommendations directly into AI-generated answers. It is the start of advertising moving inside the AI conversation. A new surface, and a new set of questions for marketers.

Every answer surface eventually grows ads. Search did it. Social did it. The AI answer was never going to be the exception.

2 min read

Taboola is turning AI chatbots into ad inventory. The company is opening the monetisation technology behind DeeperDive, its generative answer engine, to other AI companies, including those running conversational AI, chatbots and virtual assistants. The result is sponsored recommendations inserted directly into AI-generated answers, with Taboola handling the ad sourcing, targeting and billing.

The example Taboola gives is plain. A user asks an AI about buying a home and the answer can surface a targeted mortgage ad alongside the help. DeeperDive already generates tens of millions of AI answers a month for more than 7 million users, and USA Today alone has logged more than 25 million questions since launching it.

Why it matters

For two years the open question about AI answers has been how anyone makes money from them. This is one concrete reply. Ads move inside the conversation, blended into the response the user asked for. That creates a new place to buy attention and a new place where your brand can show up, or be shown up next to.

7 million

Monthly users of Taboola's DeeperDive answer engine, the inventory now opening to ads inside AI responses

For Australian marketers this is early and worth watching rather than rushing. The pattern matters more than this one product. As ads enter AI answers, the line between the organic answer and the paid placement gets blurry, and that is exactly the sort of blur that erodes trust if it is handled badly.

What to do about it

Watch where your category shows up in AI answers before you pay to appear there. Ask the tools your customers use what they say about your space. You cannot plan for a surface you have not looked at.

Do not abandon earned citations for paid ones. Being the source an AI quotes for free is worth more than buying a slot next to the answer. Paid placement is a supplement, not a replacement.

Treat early AI ad inventory as a test budget, not a core channel. It is new, it is unproven and the measurement is immature. Spend small, learn fast and keep your back pocket full.

Mind the trust line. If your ad shows up disguised as a neutral answer, the short-term click is not worth the long-term suspicion. Customers already distrust unattributed AI answers.

The AI answer is becoming a commercial surface like every surface before it. The smart move now is to understand it, not to pour budget into it before anyone knows what it returns.

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Filip Ivanković
The Debrief / From Filip Ivanković
One every morning. Six months in, you'll see the patterns most don't.
Strategy, benchmarks, and what's actually moving in Australian marketing. Four-minute read. The reps compound.
Filip Ivanković·Founder, New RebellionAboutLinkedIn