Last Monday, OpenAI and Shopify announced a new partnership enabling Shopify and Etsy merchants to sell products directly through ChatGPT conversations via the new “Instant Checkout” feature. This marks a striking shift in how e-commerce may operate: rather than redirecting users to a storefront or external site, purchasing could become embedded in AI-driven conversations.

AI is increasingly blurring the line between asking questions and making purchases. What begins as brainstorming – finding recipes, asking for advice, or planning a new skincare routine – can now end with a completed transaction in the same chat window. With this shift, major retailers and emerging brands alike will soon find themselves just a prompt away from their customers.

Ottawa entrepreneurs selling online now have a new opportunity – and a few new challenges. Instant Checkout could boost sales, but it also raises questions about data, liability, and visibility. Having worked with founders in our law clinic, here’s how I see things unfolding.

The Upside: Seamless Commerce & More Channels of Reach

Imagine a shopper asking ChatGPT: “What are good waterproof jackets?” and being able to click “buy now” inside the chat without any redirects. That seamlessness could reduce drop-off in the sales funnel. For young brands, fewer lost clicks mean more chances to turn casual interest into a loyal customer base, and to drive that momentum back to their own websites.

For many entrepreneurs, search engine optimization (SEO) and paid ads are at the centre of their marketing strategies. Instant Checkout gives entrepreneurs an additional tool to boost visibility and drive traffic to their online stores. Being discoverable in the AI space brings a new route to reach potential buyers, and deliver better results for your business. The announcement indicates Shopify will feed product metadata (pricing, inventory, images, and variants) into ChatGPT’s systems so that items become instantly discoverable.

Shopify states that merchants will still be the “merchant of record,” own the customer relationship, and decide whether to route users via Instant Checkout or to their store. Merchants will see all orders directly in their Shopify admin, complete with attribution.

So, for an Ottawa-based start-up selling via Shopify already, this is not necessarily displacing your existing store – it’s an additional channel. But “additional” doesn’t mean “no effort required.” While the convenience for shoppers is clear, start-ups need to be mindful of the hidden complexities this new channel introduces, from data and privacy concerns to operational and legal obligations.

Legal and Practical Risks to Monitor

The new system charges merchants a small fee per completed transaction. While Shopify did claim that their fees will be transparent, it remains unknown what that fee will look like for Canadian businesses. Start-ups must understand how much margin they give up in this channel.

Some commentators already caution that what seems “neutral” may become a pay-to-play arena, where certain merchants get better placement or sponsorship in ChatGPT responses. Merchants with larger marketing budgets or better AI-optimization might dominate visibility.

Aside from fee structures and revenue shares, start-ups should pay attention to data and privacy concerns. Since transactions happen through ChatGPT, third parties (OpenAI) may have access to customer metadata, purchase history, and user behaviour. Start-ups engaging in e-commerce via Shopify should ask how this new channel might affect their privacy obligations under PIPEDA.

Finally, start-ups should consider how liability, returns, and dispute handling will work in this new AI-driven environment. If a customer makes a purchase through ChatGPT, who is responsible when a product arrives late, defective, or not as described? While Shopify remains the merchant of record, the conversational nature of these transactions may blur expectations about who the buyer is actually dealing with: Shopify, OpenAI, or the brand itself. Clear terms of sale, accessible refund policies, and well-defined dispute resolution processes will be critical to maintain consumer trust and limit exposure to potential claims.

The Road Ahead

For Ottawa start-ups, Shopify’s integration with ChatGPT represents both a new frontier and a test of readiness. The opportunity to reach customers directly through AI-driven conversations could redefine how small businesses grow – but only if founders prepare strategically. Staying informed, safeguarding customer data and clearly defining terms and responsibilities will be key to navigating this next phase of digital commerce. The key for start-ups is to navigate these changes thoughtfully, and use this shift as an opportunity to build trust and visibility in an evolving marketplace.