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Chatbots Behaving Badly™

Is Your Brand Flirting With AI?

By Markus Brinsa  |  March 13, 2025

Sources

Advertisers have relied upon search engines for decades to target consumers using methodologies like pay-per-click (PPC) advertising and search engine optimization (SEO). The world is evolving as consumers are moving towards using AI-based chatbots instead of conventional search engines. The transition brings with it a fundamental challenge—unlike search engines, AI-based chatbots neither show ads traditionally nor are programmed by default with the intention of giving priority to paid content. This brings us to a fundamental question—how can advertisers target their audience effectively within a world dominated by AI?

The answer lies in AI-native advertising, a new paradigm in which brands must establish their space within the data universe upon which the AI relies.

As opposed to search, where the results are ranked based on keyword bidding, the answers given by the AI chatbots are drawn from their data sets, real-time lookups from the world outside, and API calls. Advertisers must now adapt their strategies based on the new paradigm of digital discovery.

AI-Native Sponsored Content

AI-native sponsored content is advertising within the context of the AI-created message rather than as separate ads. It is a less interruptive and more natural way of engaging users with product, service, or recommendation suggestions.

For this to occur, advertisers would need to partner with AI chatbot providers who facilitate paid placement within pertinent queries. This may be done through various means.

Content Ranking Impact – Just as search engines prioritize paid search results, AI-based chatbots can be programmed to prioritize sponsored answers when the context is suitable for the user's question.

Contextual AI Ad Inserts – When a user searches for the best holiday destinations, the AI bot may not just give generic suggestions but also include sponsored holiday packages or paid-for visibility for the airlines.

Integration with Conversational Commerce – The chatbots could be programmed to enable direct purchases within the chat experience itself with a smooth transaction path from recommendation to checkout.

Technical specifications for natively embedded sponsored content within AI include the capability for paid question-and-answer content within their algorithms. Advertisers would be provided with ad placement APIs formatted to feed the AI with sponsored content while ensuring the answers remain proper and unbiased. The AI companies would also be required to design advertising governance guidelines to avert ethics and legal complications arising from transparency and disinformation.

Branded content within Training Data for AI

AI algorithms are trained from vast data sets but are not typically trained directly from traditional ad copy. They are trained from sources like books, articles, academic journals, and publicly available web pages. Brands needing their content to generate answers through AI need to include their content within these data sets.

In order to do this, advertisers need to produce authoritative content of high quality that the AI algorithms will automatically integrate into their answers. This involves

Technically, brands must include schema markup (structured data) within their sites to make their content better interpreted and retrieved by AI systems. Brands also increasingly employ retrieval-augmented generation (RAG) models, which draw data from authoritative sources in real-time. To capitalize on this, brands must make their content accessible through real-time API feeds capable of being queried by AI systems.

Affiliate and Commerce Integration

With the growing commercialization of AI chatbots, transactional and affiliate monetization within the suggestions provided by AI is possible. Instead of simply providing data, AI can enable direct purchases, just like search engines drive traffic toward e-commerce websites through affiliate links.

To leverage this, advertisers should integrate with AI chatbots through:

Affiliate API Feeds – Brands can provide real-time prices and inventory levels and buy links through structured APIs dynamically accessible by AI chatbots.

Conversational Plugins for Commerce – The AI platforms can be integrated with websites such as Shopify, Amazon, or direct e-commerce websites to complete transactions.

Dynamic Personalization – AI-powered commerce experiences can be tailored based on user behavior, search patterns, or past interactions.

Technically speaking, affiliate tracking mechanisms are essential to attribute conversions correctly. Advertisers must utilize UTM tracking within AI-generated links and partner with AI providers to create commerce-conducive API integrations where user purchases can be made seamlessly within the context of chat interfaces.

Real-time API Access for Advertisers

Advertisers must also ensure real-time API accessibility for the AI chatbots to provide the most current prices, product status, or service updates. This allows the AI systems to use live data rather than solely static training data.

Advertisers must develop RESTful APIs that expose structured data, including prices, product descriptions, stock quantities, and promotions, to enable this. [1]

Advertisers must also apply rate limiting and query optimization so that AI chatbots can retrieve data efficiently and not overload the systems.

AI Retrieval Optimization (AI SEO)

Just like websites are ranked higher with conventional SEO for search, AI SEO is becoming the way content is prioritized within the answers given by AI chatbots. Since AI algorithms rely on information retrieval techniques, brands must optimize their content for discovery by means of AI.

Key strategies for AI SEO are

Technically, AI retrieval systems are vector databases and embeddings-based for processing natural language. Advertisers need to make their content tokenization-friendly, i.e., semantically structure their content such that the AI model can extract the most relevant pieces.

Why AI Chatbots Haven't Monetized Search (Not Yet)

AI chatbots operate differently from search engines, which generate revenue through paid rankings and keyword bidding. There are several reasons why chatbot developers haven't aggressively monetized search within AI.

User Experience Problems - The chatbots are designed to be helpful and friendly. Invasive ads could undermine the user experience.

Lack of Standard Ad Model - There is not yet a standard monetization model for ad placement for AI chatbots as there is with pay-per-click search.

Ethical and regulatory hurdles - The potential for biased and deceptive AI-generated replies makes monetization challenging.

Alternative Monetization Strategies - Instead of traditional ad-based monetization, developers could target monetization through API access, enterprise licenses, or subscription-based approaches.

The Future of AI Advertising

The shift towards marketing through AI is unavoidable. AI chatbots are transforming the way consumers find information, make purchases, and interact with brands. With developers looking into monetization strategies for their chatbots, advertisers need to act proactively and get their brands placed within the ecosystems of AI through structured data, real-time APIs, and AI-native content strategies. The future of advertising with the help of AI will be a hybrid model with sponsored AI answers, real-time data accessibility, and integrations with commerce existing side by side with one another in a way that balances user trust and monetization. Brands that transition early will have a competitive advantage within the AI-first digital world.

About the Author

Markus Brinsa is the Founder and CEO of SEIKOURI Inc., an international strategy consulting firm specializing in early-stage innovation discovery and AI Matchmaking. He is also the creator of Chatbots Behaving Badly, a platform and podcast that investigates the real-world failures, risks, and ethical challenges of artificial intelligence. With over 15 years of experience bridging technology, business strategy, and market expansion in the U.S. and Europe, Markus works with executives, investors, and developers to turn AI’s potential into sustainable, real-world impact.

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