Chatbots At Checkout

Plus: OpenAI goes musical, Outlook gets Copilot, AIs simulate survival.

Here’s what’s on our plate today:

  • 🤖 AI agents start buying—not just recommending.

  • 🧠 OpenAI goes musical, Outlook gets Copilot, AIs simulate survival.

  • 💡 Roko’s tip: Optimize your data for AI shoppers.

  • 🗳️ Poll: Would you let a bot shop for you?

Let’s dive in. No floaties needed…

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The Laboratory

The rise of agentic commerce

Photo credit: TechCrunch.

In 2004, Mark Zuckerberg changed the meaning of social media with Facebook. When it was first launched, no one could have predicted that someday users would spend more time debating politics, posting images and videos on social media platforms than in the real world. However, in 2025, that is a reality, and social media addiction is a real affliction for many.

However, while social media continues to reshape social, political, and economic structures, another technology threatens to upend the existing apparatus. Since 2022, artificial intelligence has been at the center of technological advances and debates around its use cases, impact on society, and politics. While headlines focused on these shifts, chatbots continued to weave their way into daily lives, and now they are prepared to bring about a tectonic shift in how users access information and make decisions.

According to OpenAI, people are turning to chatbots for practical guidance, seeking information, and writing. Of the 700 million weekly active users, around 70% of the conversations are not personal queries and revolve around decision-making, like planning vacations and seeking emotional support

This makes them the perfect assistant not just for users, but also for e-commerce platforms. However, it is not just the ability of chatbots to recommend products that makes them great promoters; the industry as a whole seems to be preparing for chatbots to become the perfect salesman.

OpenAI’s ‘instant purchase’ push on ChatGPT

In September, OpenAI made updates to integrate shopping directly into ChatGPT, marking a turning point in the evolution of e-commerce, where conversational AI is beginning to replace traditional search-driven retail.

The company recently unveiled an Instant Checkout feature that lets users purchase products directly within ChatGPT, without leaving the chat interface. This feature is powered by the Agentic Commerce Protocol, a payment standard co-developed with Stripe, which OpenAI has open-sourced to encourage adoption across the retail ecosystem. The rollout begins with Etsy sellers and will soon expand to over a million Shopify merchants, including major brands such as Glossier, Skims, Spanx, and Vuori.

By allowing users to search, evaluate, and buy in a single interaction, OpenAI is transforming ChatGPT into a kind of digital shopping assistant, one that could soon act autonomously to make purchases on behalf of users.

For users, it means that they will have more personalized, context-aware shopping experiences, where AI understands preferences, budgets, and even past behavior to recommend products organically rather than through paid placements.

Beyond OpenAI, the development aligns with a broader shift in the online shopping market.

Visa, Mastercard push for agentic shopping assistants

Photo credit: Getty Images.

According to reports, Mastercard and Visa have both announced new capabilities allowing AI agents to not only suggest or recommend products but to research, negotiate, and complete purchases automatically, once users set preferences and permissions. This marks a shift from AI as an assistant to AI as an autonomous actor in commerce.

Mastercard’s ‘Agent Pay’ is built around a new architecture with agentic tokens (similar to the tokenization of credit cards) and verification/authorization systems so that AI agents can act securely and transparently.

Similarly, Visa announced an ‘Intelligent Commerce’ initiative that focuses on enabling AI models (like ChatGPT or others) to transact using delegated authorization of Visa credentials (tokenized) so agents can act within user-defined bounds.

Visa’s focus is on developer accessibility and security, offering APIs, tokenization, and robust identity verification to ensure users can define spending rules. Mastercard, on the other hand,  is emphasizing traceability and trust, requiring agent registration and verified digital identities so that every AI-driven transaction remains auditable.

While the payment gateways have taken different approaches, their strategies could potentially redefine how online commerce operates. Their strategies could potentially allow users to offload routine shopping tasks like ordering groceries, restocking essentials, or comparing prices to AI agents.

Additionally, AI agents can also shape user perspectives on vendors based on availability, price, and credibility, and then execute payments securely within user-defined parameters. All these could change not just how commerce is conducted in the online space, but also how vendors and producers market their products.

What it means for online commerce

The multi-fold push signals the dawn of ‘agentic commerce’, where AI systems manage the entire shopping lifecycle, from discovery and decision-making to payment execution.

For businesses, it means adapting to a world where AI agents, not humans, become primary customers, changing how merchants structure data, optimize pricing, and advertise. However, challenges persist. Fraud prevention, transparency, and fairness are critical as these systems gain autonomy. There are also concerns about user trust, bias in merchant selection, and competitive imbalances between advanced and less capable AI agents, all of which must be addressed for this technology to mature responsibly.

As for businesses, the very model of online advertisements might shift from vying for a spot on Google’s search results to advertising inside user chats.

A clear example of this shift was seen in May 2025, when Bloomberg reported that Google’s AdSense advertising network started supporting ads inside users’ chats with some third-party AI chatbots.

The report said that Google has begun rolling out the feature following tests with AI search startups iAsk and Liner.

To understand the shift, imagine instead of Googling ‘best noise-canceling headphones’ and clicking through affiliate links or product pages, a user might ask ChatGPT, which provides ranked suggestions and a direct recommendation in the chat. Now, if the user can not only research the product but also act on the impulse of purchasing it within the app, it would remove the need for businesses to advertise on Google.

While Google is responding by integrating AI into its search products in a bid to retain control over queries, businesses that rely on Google Search traffic for leads or sales may see a decline in organic traffic as users increasingly turn to chatbots for direct answers or recommendations.

As such, businesses will have to shift their focus away from SEO strategies, search ads, and referral marketing, and towards presence for AI-first discovery.

Additionally, to make the best of the new channel of sales opened by AI chatbots, businesses will have to ensure their inventory, pricing, and product data are optimized for AI discovery.

In essence, the emergence of AI-driven commerce is reshaping how businesses engage with consumers, compelling them to adapt to new technological paradigms.

Preparing for the AI economy

If the vision of online commerce that has been put in motion by companies like OpenAI and Google materializes, it could upend not just jobs in customer service and customer support. But also businesses that fail to realign their vision of digital strategies.

This realignment, however, opens up new opportunities in areas where companies will look to ensure their product data is structured and accessible to AI agents, potentially requiring integration with new protocols and platforms.

When social media platforms first emerged, no one could have predicted the kind of influence they would have on political, social, and economic activities. Nowadays, social media influencers, if judged solely by their financial rise, add more value to an economy than many other professionals.  The same may be true for a future where chatbots recommend, purchase, and pay for online purchases.

Roko Pro Tip

💡 When optimizing your business for AI-first commerce, ask: Is our data structured enough for agents to find, evaluate, and buy?

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Prompt Of The Day

”Act as my personal AI shopping assistant. I’m looking for a [product type] under [budget], with [specific preferences]. Recommend 3 great options and explain your reasoning for each.”

Bite-Sized Brains

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